Google, now Alphabet, started out as a search engine and is today a multinational conglomerate with a market cap of over $500B. The company has expanded well beyond the original core search engine business and now owns multiple products and divisions like YouTube, Google Maps, Chrome, Android, and new hardware products.  GV (formerly Google Ventures) is the organization’s venture arm and has made investments in companies like Uber, Slack, HubSpot, 23andme, and many others.

Back during the 90s dot-com era, there was a Boston-based company that was like an earlier version of what Google is today.  It was an early adopter that pushed the limits of the internet, which at the time was the new frontier.  This company played a major part in laying down the foundation for what the internet is today.  

The company was revolutionary.  It had a powerful search engine, many different innovative products, Eric Schmidt’s attention, and a venture arm.

This company was CMGi in Andover, Massachusetts. 

Yes, this is the same company that had the original naming rights to the home of the New England Patriots, which at first was known as CMGi Field.

Unfortunately, along with the entire industry, the company had a rapid rise and then a massive collapse and became the poster child for the dot-com era.

Regardless of the stigma placed on the company, it is interesting to look back at all the innovative companies and products CMGi built or invested in.  At its peak, the company had over 70 investments, 20 subsidiaries, 5K employees, and $1.5B in annual revenue.  Its market cap was $41B and ranked somewhere around No. 7 - 9 in the world in terms of aggregate traffic to all of its properties.  

I’m fascinated by the history of Boston tech, so I decided to take a dive into the company’s history by interviewing David Wetherell, who was the Chairman and CEO of CMGi.

The History of CMGi

The company was originally known as CMG Information Systems before the name was shortened to CMGi. Wetherell became Chairman, CEO, and President after a leveraged buyout of the company in 1986.  CMGi’s core business was focused on selling mailing lists of university faculty and information buyers to educational and professional publishers.  After taking over, Wetherell built up the company’s revenue and market share, and the company went public in 1994.  Shortly after its IPO, Wetherell founded BookLink Technologies, a web browser company, which was sold to America Online for an all-stock transaction that yielded $72M for CMGi from an initial $900K investment.

The proceeds from the sale of BookLink allowed CMGi to focus on a two-pronged strategy. It would incubate its own startup internet companies and also have an investment arm, CMG @Ventures, to fund other early stage internet companies.  As the business and its portfolio grew, CMGi became a NASDAQ 100 company and market leaders like Microsoft, Intel, and Sumitomo held minority positions in it.

CMGi’s portfolio included companies like AltaVista, Engage, Lycos, GeoCities, Raging Bull, NaviSite, Furniture.com, MotherNature.com, MyWay.com, Snapfish, Yesmail, and many others.   (We’ll have a slideshow on VentureFizz tomorrow digging deeper into the portfolio and how these companies were precursors to many of today’s major web products.)

In 2000, CMGi was working with Eric Schmidt, then-CEO at Novell along with Sun Microsystems and Compaq on a new initiative called CMGion.  Each partner agreed to invest $20M and build a unified, global, internet-based network service, which ultimately would have been a competitor to Akamai and other Content Delivery Networks if the market didn’t collapse.

The venture arm made some great investments, but like most firms, there were ones that got away.  For example, CMG @Ventures had the opportunity to invest in the first round of capital for eBay, but they couldn’t come to terms.  eBay was profitable already, so it was looking for a pretty lofty valuation, which ended up being a small price to pay as compared to the ultimate value of the company.  

According to Wetherell, Novell and CMGi were planning a merger and Eric Schmidt would have been CEO of the combined entity but the merger was put on hold when the market crashed during the spring of 2000.  He also mentioned at one point CMGi discussed acquiring Google, but the board was against the idea.  

AltaVista

One of CMGi’s major portfolio companies was AltaVista, one of the first major internet search engines.  AltaVista was developed by researchers at Digital Equipment Corporation (DEC), and it was the Google of its time. In 1999, CMGi purchased 80 percent of the company from Compaq, which had acquired DEC, and transformed it into a web portal company to compete against Yahoo! and others.

AltaVista was set up to go public in 2000 right when the stock market crashed for tech companies, leading to the ‘internet bubble burst’, and CMGi was forced to delay the IPO. Even after the bubble had burst, AltaVista still had value and Wetherell believed that it could have enabled CMGi to remain a significant player in the internet space.  After cutting costs, AltaVista still had $50M in revenue and was break-even.  Even more valuable was the fact that AltaVista owned 50-60 key search engine patents, which Wetherell believed was worth more than what CMGi paid for the asset.

Google had serious momentum at this point and was quickly becoming the search engine behemoth that it is today. Despite challenges in the marketplace competing with Google, Wetherell argued to the board that the company should retain AltaVista because of the value of its patent portfolio, which would later yield value from Google in return for freedom to operate once it was ready to go public. The BOD was not convinced, and AltaVista was ultimately sold to Overture Services (later acquired by Yahoo!). It is believed that Yahoo! received in the vicinity of five percent of Google in exchange for the freedom to operate, which today is worth in excess of $25B.

The Fall

The dot-com bubble’s burst could have been avoided was it not for the Y2K / new millennium bug and a confluence of other factors, according to Wetherell.  There was a great deal of fear and anxiety surrounding the Y2K bug which might have caused computers to crash and perhaps a run on banks. To counter this fear, the Federal Reserve Bank flooded banks with $60B of liquidity to make sure the banks had enough cash to keep operating in the event of such a run.

Once the turn of the century occurred, and there was no run on the banks, the Fed feared that the extra liquidity would prove to be inflationary, despite the fact there were no signs of inflation. To counter this inflationary concern, the Fed raised interest rates six times in six months. This, in turn, caused the IPO market to shut off, leading to the market crash, and venture capital, the lifeline of early stage internet companies, dried up. It ended up being a perfect storm of events which maybe didn't need to happen at all and could have saved the industry from such an abrupt downward turn. 

It was a tough time for CMGi and the rest of the tech industry.  There were a lot of tough decisions. Companies folded, people lost jobs, and investments lost value.  Quickly, $20B in CMGi’s public market portfolio lost value.

Surprisingly, CMGi did survive the dot-com collapse, as they focused on a core of six internet companies, including AltaVista. Then, with the attacks of 9/11, the stock market crashed again, which put additional pressure on the company. The BOD made the decision to jettison its internet businesses, the last of which was AltaVista.

So, what is Wetherell up to now?  After retiring from CMGi, Wetherell took his background in the high tech industry and applied it to something that had more meaning for him: life sciences.  He started out as a sole angel investor, and it blossomed into an investment firm with $200M under management, called Biomark Capital.  The firm has invested in a dozen leading edge Biotech and healthcare companies, and he finds the firm’s work extremely gratifying.

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Keith Cline is the founder of VentureFizz. Follow him on Twitter: @kcline6.

Rudina Seseri is a Managing Partner & Founder at Glasswing Ventures, which is one of the new VC firms in the Boston area.  Rudina previously spent almost ten years at Fairhaven Capital, where she invested in Jibo, Celtra, CrowdTwist, SocialFlow, and Statisfy.

Rudina's new firm is focused on investing in companies where AI is at its core.  She is a very active member of the Boston tech scene and she also serves as an Entrepreneur-In-Residence at Harvard Business School. 

Keith Cline:  Tell me about your background.

Rudina Seseri:  I was born and spent my early childhood in Albania.  At 15, I took a risk, leaving my family – the most challenging thing I have ever done in my life - to attend high school here in the US. I received my undergraduate degree from Wellesley College in Economics and International Relations. My experience at Wellesley was very  meaningful not simply because of its academic strength, but because of its commitment to empowering women. I was surrounded by ambitious, intelligent women and I learned that if one applies oneself, approaches challenges strategically, and has passion, the likelihood of success is high. I don’t think it is a coincidence that its strong alumni network includes the first woman astronaut, a Supreme Court Justice, a former Secretary of State, the co-founder of BlackRock, and, most recently, the first female Presidential Nominee in US history, among others. 

KC:  What did you do for work right out of college? 

RS:  After graduating from Wellesley, I worked for three years as an analyst at Credit Suisse in the Technology Group where I caught the tech bug, and realized that the tech industry was where I wanted to be.  I did go on from there to attend the Harvard Business School (HBS) to earn my MBA.  During the time I was at HBS, I met Rick Grinnell and worked on a wireless infrastructure project for him.  He counseled me to work at a technology company which led my becoming a senior manager at Microsoft in Redmond, working in the company’s corporate development group. After working and closing a number of deals in under two years, I decided to come back to Boston and join Rick Grinnell and the team, working as a venture capitalist. We have had a long-standing successful venture career and business partnership. Almost 10 years later, it culminated in the formation of our new VC firm, Glasswing Ventures.

KC:  You started Glasswing Ventures with Rick Grinnell and Sarah Fay, what’s the company focus and how did go about naming the firm?

RS:  That’s right, Rick Grinnell and I are co-founders, and our third partner is Sarah Fay. Over the last five years, Sarah has worked closely in the startup ecosystem as an angel investor, advisor and independent board director. The three of us have decided to pursue a very focused firm strategy with a large market opportunity, investing in companies that have AI technology at their core as the enabler in multiple industry segments spanning enterprise SaaS, data and predictive analytics, security, robotics and related platforms. Our focus is on companies that intelligently solve the needs of the connected world and provide security for its ecosystem.  We’ve coined the term -  Intelligent Connect and Protect™ - to capture our strategy. 

We named the firm Glasswing Ventures after the butterfly, which of course is an appropriate symbol of transformation.  The Glasswing butterfly is also a specific type of butterfly.  It’s unique in that it has transparent wings, which allows one to see the strength of its wing's structural mechanics.  It’s a graceful creature, able to take flight, while still embodying great strength and resilience.  This is analogous to our mission, to be transparent with our founders and management teams and the broader ecosystem as we build a strong firm that will make a lasting positive impact in the market. 

KC:  What investment strategy will you be focused on at Glasswing?

RS:  We are series A investors, focused primarily on East Coast startups, with a heavy focus on Boston and NYC.  The East Coast has developed a leading ecosystem in AI across the industry segments we are focused on, which are core to our investment strategy. We are looking to work with founders to help transform their ideas into companies, and help their companies grow into industry leaders.  

KC:  When you invest in companies, what do you look for?

RS:  There is a distinct common thread across all of them – it’s the transformational role they are playing in their respective industries AND the exceptional execution by the founding and management teams.  Some of the companies I have invested in are Jibo, a clear leader in social robotics, and one of the most highly disruptive companies in the market that also is a category maker and SocialFlow, which leverages AI and deep learning to increase distribution of owned and earned content across social media platforms, Crowdtwist, a multichannel loyalty platform, among others.

KC:  What are the top traits you look for in a company or founder?

RS:  We look for founders who love to build companies not just products and are able to grow as their business grows.  There are two specific traits I look for -- agility of execution and big ideas. Of course, we love founders that have both, but, if I had to pick one trait over another it would be execution every time.  They also need to be able to pivot, course correct, in order to be able to hone in and pursue the right opportunity.  

We find amazing founders and start up CEOs from all walks of life and various career stages – from the undergrad student to the repeat successful entrepreneur with multiple exits. There is room for all of them in our highly diverse portfolio, and we are aggressively pursuing the opportunities they present to us.

KC:  What excites you about the market on the east coast, including Boston?

RS:  Boston has a significant and growing footprint in AI, which becomes the basis for creating industry-leading AI companies. Boston and the broader East Coast ecosystem is also a hotbed of enterprise, cybersecurity and robotics startups. We have leading academic institutions (MIT, Harvard, BU, BC, CMU, Cornell, RPI, Georgia Tech, etc.) that have a meaningful commitment to AI, robotics and machine learning; companies with AI as their backbone from Nuance to iRobot, and all the engineering and dev talent that the larget tech companies have in the region, in addition to an abundance of great founders, entrepreneurs and executives.  

KC:  Who do you admire or who has been the greatest mentor for you?

RS:  That has to be my Mother.  She is an incredibly strong and grounded woman.  When my Dad passed away, I was just a year old, she raised my sister and me singlehanded, while running a 3600-person company.  She raised us with the conviction and the belief that we can achieve anything we set our minds to.  It is my hope to instill those same fundamental beliefs in my daughter, so that she too knows the power behind that belief and the positive impact she can have on the world.

KC:  I noticed that you have a podcast called Next Gen Now.  Can you share the details of your show and what you cover?  

RS:  Absolutely, my podcast is focused on interviewing founders, CEOs and folks from the startup ecosystem to talk about trends and technology, discuss pet projects and to get a pulse on the industry, and how we think about and the impact of disruptive technology on our lives.  It is a pet project and I enjoy it very much, you can tune in here at Next Gen Now.

KC:  Outside of being a VC, what are your personal interests or activities? Are you involved in any charitable organizations?

RS:  As the Co-Founder of Glasswing Ventures, and the mother of my three-year-old daughter, I lead a pretty busy life.  I do very much enjoy being an Entrepreneur in Residence at Harvard Business School, where I meet with students about the companies they are founding, and discuss careers in venture with them.  It’s great to be able to contribute and give back to the school, and still have a pulse on the market and feel the excitement at the university level. I’m also on the Board of Overseers for Boston Children’s Hospital, which is doing incredible and progressive work that impacts the lives of thousands of children. It is a wonderful and constant reminder and inspiration in my life about how we can contribute to the lives of others.

KC:  What was the last book that you read?

RS:  It was a wonderfully funny novel called The Rosie Project by Graeme Simsion about an endearing geek who develops a model for finding a wife.  Definitely a laugh out loud kind of book.

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Keith Cline is the founder of VentureFizz. Follow him on Twitter: @kcline6.

David Chang is an entrepreneur and angel investor with product, marketing and software development experience at 5 startups/acquisitions. He has been part of the operating team at some of Boston's most successful companies like edocs (acquired by Siebel), TripAdvisor (IPO), m-Qube (acquired by Verisign) and WHERE (acquired by PayPal).

In the past, there wasn't a very known or active angel community in Boston.  Today, there are many active angels who are not only writing checks, but they are also mentoring entrepreneurs.  David's presence in the Boston tech scene is a great example of this shift and how things have changed since 2010 in Boston.  As you'll notice by reading below, he has done a lot in terms of paying it forward.

The image above is from the PayPal Boston office ribbon cutting ceremony back in 2013 with (starting from the left): Mayor Thomas Menino, Gregory Bialecki, Walt Doyle, and David Chang.

Keith Cline:  Tell us about your background.

David Chang:  My first memory in life consists of a drab green couch against the backdrop of a white room. I was three years old, and I remember sitting in a New York hospital waiting room on the day of my sister’s birth. Since my family had just moved from Taiwan to the U.S., all my subsequent memories are of growing up in a typical suburban neighborhood on Long Island. While still in high school, I spent six weeks in an explorations program at Cornell University, and after that, I couldn’t see spending my college years anywhere else. When the time finally came, I crammed everything I could into a hand-me-down ‘79 BMW and drove the 280 miles to school.

During my sophomore year, I met with my faculty advisor “guidance counselor” to work through the dilemma of choosing a major. Since I wanted to eventually go to business school, he suggested that I focus on a technical discipline since there would be plenty of time to pick up the business side later. For me, it was the best advice ever. I ended up concentrating on computer science since I’d been playing with computers like the Commodore PET, TRS-80, and Apple IIe for almost as long as I can remember.

KC:  What did you do after graduation and why did you go back to business school at HBS?

DC:  After 38 rejections during my senior year, I landed two job offers from very different places. The first offer was to join Oracle, a west coast tech company, as a business analyst, and the second offer was to join Goldman Sachs, an east coast investment bank, as a programmer. Undecided, I spent a week in California during spring break to test the waters to see if I could live there, and I just couldn’t see myself doing it.

I joined Goldman Sachs and started in the New York headquarters, just 40 miles from where I grew up, in a role bridging technology and finance. The work brought me around the globe as I packed my bags and headed to Asia and Europe. I never did get my bearings in Hong Kong, but soon felt equally at home in New York City’s Greenwich Village, Tokyo’s Roppongi, and London’s South Kensington. During my seven years at the company, I wore a few hats: programmer, technical architect, database admin, team manager, market researcher, accounting specialist, product development manager, global coordinator, and finally VP of Technology. There were days when I got into the office at 5am because I couldn’t wait to start the day. Although I was thrilled with my job, I never shook my fixation on getting an MBA.

After a painful process of multiple years of applications and rejections, I finally got into a couple of schools on my final attempt. I eagerly sent the tuition deposit to Harvard Business School, but reluctantly submitted my resignation letter. I procrastinated clearing out my office, which looked out onto the World Trade Center. I finally was able to focus when I reminded myself that the relocation to Boston would only be two years of my life. Little did I know that I would be here 17 years later.

KC:  Can you share your experience from your time at edocs?

DC:  Kevin Laracey, the CEO of edocs, may still remember my complete disruption of his company’s info session during Boston Trek, a multiple-day visit of local tech companies for second-year business school students. I showed up over 30 minutes late - not the best way to make a first impression. I somehow recovered from that initial stumble and convinced Chris Gardner, director of product management, to have a follow up meeting with me. The timing was not good - the 2001 internet bubble had just burst. Although they didn’t have an open position at the time, I just kept hounding Chris until I got a job offer just weeks before graduation.

As a former software engineer, I had a bumpy transition into product management. During my first six months, my hand was repeatedly slapped by an engineer when I fell back into the mode of trying come up with the solution, rather than defining the problem. I eventually settled into a good rhythm of a typical day, and focused on three main parts of the job: product management (being “CEO” of the product and working with the internal team making the game time tradeoffs), product marketing (writing business cases and putting together externally facing materials), and sales support (the raw blocking and tackling of selling - finding the decision maker and closing the deal). In the end, I learned a ton from co-workers like Rob Orgel (COO Quattro/Apple), Jim Moran (North Bridge), Mark Quinlivan (CEO of Confer), Jed Rice (SVP Paydiant/PayPal), Melinda Smith (CFO Paydiant/PayPal), and Mike Massaro (CEO of Flywire) over three years at edocs. I could not have asked for a better first real experience at a venture-backed startup.

KC:  You joined TripAdvisor in 2004.  How many employees did they have then and what was your role?

DC:  I remember how jarring it was to transition from edocs, an internet enterprise software company, to TripAdvisor, a consumer internet company. At edocs, we’d launch a new version of the software once a year and scramble to launch a point release every few months. I was shocked on the first day when Steve Kaufer, TripAdvisor’s CEO, asked me to launch a new feature before the end of the week. It turned out that we’d release new stuff EVERY week. As the company’s first dedicated product manager, I worked on ways to make it easier for travelers to plan their trips: introducing new ways to search for hotels, running A/B tests to optimize the site, getting into the consumer’s head through surveys and focus groups, and negotiating deals with vendors.

Compared to the juggernaut TripAdvisor is today, the team was very lean when I was there. I recently found my first pay stub, which lists my employee ID number as #33, but I’m sure we were smaller than that. We had one person in sales, Robin Ingle, who is still at the company (contrast that with this recent photo of her sales team). Shortly after I joined in 2004, we needed to hire a merchandising manager and quickly found two great, but very different, candidates: Adam Medros and David Krauter. Steve finally suggested that we hire them both, and I thought that was the most insane thing ever - how could we possibly hire two people and figure out how to define roles that would make sense? It turned out I was wrong (not surprisingly). Twelve years later, they are on the leadership team of the now public company (NASDAQ: TRIP): Adam is SVP of Global Product, and David is the President of several TripAdvisor properties. Steve figured out how to create meaningful roles.

KC:  What brought you to m-Qube, which was acquired by Verisign?  Can you share some of the details from your time there?

DC:  I decided not to join m-Qube. I called Chris Gardner, the hiring manager at m-Qube and my former boss at edocs, to decline the offer but got his voicemail instead. I chose not to leave the message, and by the time I called back later that day, I changed my mind. The combination of working with a great team that I used to work with, but in a new explosive industry, tipped the scales in favor of joining m-Qube. In the year I joined, we did $6M in revenue, then the following year did more than $80M. It was a time of insane growth - it seemed like each week, the new hire orientation got bigger and bigger.

As a product/tech guy, it was unnerving to focus on just product marketing. For the first time in my career, I no longer had a direct hand in deciding what got built. I purposely chose to sit in the bullpen with the 4-person product management team in order to overhear what they were working on. What’s more, we lost our corporate marketing person just before I joined, so I ended up taking on a true marketing role for the first time in my career. It seemed as though every month brought an entirely new challenge due to the explosive growth. When our CEO Jeff Glass announced that Verisign was acquiring the company, I remember thinking that we still had so much to do. My time there was a blur, and I got to work with so many talented people who have gone on to make such a mark on other parts of the industry. Again difficult to name all, but some included Jim Crowley (CEO of Skyhook), Andy Miller (CEO Quattro/Apple), Mike Troiano (CMO Actifio), Jennifer Lum (Co-founder Adelphic), and Lars Albright (CEO SessionM).

KC:  You started your own venture backed company called Mobicious?  What was the idea and what happened?

DC:  I had no intent on leaving Verisign/m-Qube, but when I met George Grey, we saw an opportunity to create for mobile consumers a media app store (an “app store” two years before Apple launched its app store). It was super risky, but it was a unique chance to leverage what I learned at TripAdvisor and m-Qube. Over the course of a weekend, I quit my job at Verisign, joined forces with my co-founder at a new startup without a name, and had a daughter. Lots of change in 48 hours. Over the next couple of months, we refined the business plan, pitched to VCs, and landed a $4M A-round during the summer of 2007 to build out the company. I was so glad to recruit my former m-Qube marketing team Aimee Anderson and Lauren Romeiro and former TripAdvisor lead developer Matt Conway to join the company.

Just one month after we landed our funding, we discovered that consumers were gravitating towards free media and creating their own content. As a company, we soon pivoted to create SnapMyLife, a mobile photo sharing service where people could quickly post pictures and discover images from around the world. By mid-2008 (two years before Instagram’s launch), SnapMyLife users from 190 countries around the world were sharing photos, but we couldn’t figure out a way to monetize. We waffled back and forth between different use cases - should we focus on private sharing (e.g., sending pictures of your kid to your mom) or public discovery (strangers sharing photos with each other)? Switching back and forth, going from guardrail to guardrail, between these extremely different features was a killer. Never do that.

As we struggled to find a new direction for the company, we had to significantly cut the burn rate and switch gears. I ended up laying off half of the team, including myself, to give the company a shot to succeed in pursuing a B2B strategy selling to media companies. Long after I left, we found an acquirer for the company, but for pennies on the dollar. Not the brightest day as an entrepreneur, but such valuable lessons for me during this journey.

KC:  What brought you to WHERE, which was acquired by PayPal, as the company’s VP of Product?  How did your role evolve over time?

DC:  As I wallowed for a week in the summer of 2009, wondering if I could get a job again, I blanketed my network and sent emails to about 30 former colleagues, a dozen VCs, and a handful of headhunters. One of them included Noam Bardin, the CEO of a little known, but cute app called Waze. It sounded like a fun opportunity, but I didn’t want to move out to California. David Beisel, who I first chatted with when he was career soul searching as a grad student, connected me with Walt Doyle. We chatted about a VP of product role that combined a number of things in my past: B2C and B2B, mobile and web, and location.

Joining WHERE was like joining a new family. Unlike my previous startups, I really didn’t personally know anyone on the team. But what a team it turned out to be! I got to work alongside Dan Gilmartin, Ivan Mitrovic, Doug Hurd (Co-founder clypd), Niall Hawkins (CFO Evertrue), Ron Braunfeld (VP Pingup), and Jerry King (COO Vets First Choice) all under one roof. We had a super talented product team of Joshua Summers (Co-founder/CEO clypd), Arik Keller (CPO Confirm.io), Jim Caralis, and Nataly Kogan (CEO Happier), each of whom has since launched his or her own company. With superstars like them, my product role quickly morphed into other areas, and I took on corporate development to focus on the growth or acquisition of the company. I took on a general operating role after the PayPal acquisition, and led the Boston office after Walt’s departure.

Soon after, I co-founded the Start Tank innovation space, which brought me closer back to the world of early stage entrepreneurship and startups. I look back fondly at some of the earliest startups at the Start Tank and how they’ve grown: Polina Raygorodskaya (CEO Wanderu) and Amanda Curtis (CEO Nineteenth Amendment). Things came around full circle just as I left PayPal in a public way and the Paydiant acquisition was announced. Paydiant’s founders were none other than Kevin Laracey, Chris Gardner, and Joe Paratore (who passed away in 2012) who I worked with at both edocs and m-Qube, and it was so exciting to see their success and continue Boston’s leadership for a major tech company.

KC:  How did you get into angel investing and what are some of the first companies that you backed?

DC:  My first angel investment was an accident. During an interview with a startup I was considering joining, I ended up writing a check rather than pursuing a job offer. You’ve got to love the unpredictable nature of these chats over coffee - you never know who’s selling and who’s buying. Shortly after the WHERE/PayPal acquisition, I wrote my second angel check in Crashlytics, which Twitter later acquired. I still have my meeting notes during my deep dive with Wayne Chang and Jeff Siebert over lunch at Neptune Oyster using my checklist/framework. WHERE actually sponsored the drinks night at the Beehive where Wayne crashed the event and met Jeff, so the ROI on that night is off the charts.

From 2012 to 2015, I made a slew of angel investments, many of them alongside extremely knowledgeable operators and investors. Today, I’m lucky to share ideas and leads with Shereen Shermak, who has discovered some incredible founders.

KC:  What sectors of technology, industries, or trends are of interest to you?

DC:  My startup experiences have been in web/mobile software ventures in both B2C and B2B, so I try to stay in that lane. I prefer investing in startups in fields such as software, digital media, travel, or payments where I have deep knowledge and/or contacts to give the founders a competitive edge. In the early stages, it’s so beneficial to have frequent contact with founders, so I tend to stick to local startups at the seed stage.

My primary motivation for angel investing is strengthening connections and leveraging areas of existing expertise. The potential financial return is obviously a factor, but it’s not the first criteria I use when deciding which founders to work with.

KC:  You are a very active investor in Boston companies, having invested in over 35 companies.  What excites you about the current market in Boston?

DC:  Jeff Bussgang has a great presentation of the Boston startup ecosystem, which includes clusters of excellence and emerging microclusters. I’m excited about these industries and feel strongly that we should double down on areas where we have a competitive advantage. It’s an interesting time to be in startups since the venture capital industry is also changing. Not only has the amount of capital required to launch a company been slashed, there are more kinds of capital available through syndicates and how VCs are embracing a network-model by involving skilled entrepreneurs/operators as part of their firms.

Lately, I’ve been fascinated by how founders get matched with the right set of investors and been thinking about ways to help hundreds of startups, not just the handful that I personally invest in. That’s one of the drivers behind PersonalVC, a passion project that I’m working on with Dan Deac and Stipe Ivan Latkovic.

KC:  What companies in Boston, outside of your portfolio, do you find interesting?

DC:  I love that Boston has leadership in fields like life sciences and healthcare, and I wish I knew more about other strong areas such as ed tech and robotics. I recently spent two hours with Helen Greiner of CyPhyWorks and was blown away by what they’re working on. Like many others, I’ve been paying attention to the next wave of startups where software meets hardware: iOT and artificial intelligence. It’s impossible to predict where it will all go, but with drones in the air, self-driving cars on the ground, and Terrafugia flying vehicles, it promises to be an exciting future for startups in Boston.

KC:  Greatest misses - what company(ies) have you passed on that you wish you hadn’t?

DC:  Investors circles are small, and we end up seeing a lot of the same opportunities. In the end, founders need to find the best fit, so I’ve passed on a number of great entrepreneurs where I didn’t know the space and felt I couldn’t help. Matt Barba and Frederick Townes of Placester gave one of their earliest pitches at the WHERE office, and I didn’t invest. My former board member Ryan Moore led the seed round for DraftKings, and I still have the original email of the drumming up interest for them.

It’s hard to fight FOMO, but as an investor, you have to stick to your investment thesis and feel fine when you pass on what turns out to be a great opportunity.

KC:  What are you personal interests or activities?

DC:  I have always loved photos and digital media, as my 450GB Photos Library has forced me to upgrade my Mac multiple times. My dream room in the house would be a media room with a ridiculously big screen and great sound. Outdoors, I’m a big fan of biking to get around town, and I’ve been biking to everything lately. In fact, in the first half of the year, I did two dozen workshops, events, and speaking engagements that were within biking distance of home - weather notwithstanding. Lastly, I wish I got onto the ski slopes more often. I somehow squeezed in 25 ski days one year while maintaining a full-time job. That’s not going to happen again.

KC:  What type of music do you like?  

DC:  My music playlist is embarrassingly skewed to 80’s new wave “alternative.” Growing up, I spent a ton of time making mix tapes on cassettes, which are probably sitting at the bottom of the closet. I am so excited that almost all these songs are now available in a digital format. Love live the 80’s!

KC:  Are you involved in any charitable organizations?

DC:  I spend about one day per week devoting time to non-profit and industry organizations that intersect with my professional passions. In my role as Rock Center Entrepreneur-in-Residence at Harvard Business School, I mentor college students and graduate-school level students with their ideas and careers. I quickly forget that I’m twice the age as many of the students that I work with (note to self: do not buy beers at lunch with college students). As a longtime committee member for The Ad Club’s Brandathon, where Silicon Valley meets Mad Men, I get to witness the collision of two different worlds. My longest tenure has been with MITX as a board member, which gives me a unique opportunity to work with people across the innovation ecosystem.

This past summer, I was host committee co-chair for the BUILD Boston Entrepreneur Games along with John Barros, the City of Boston’s Chief of Economic Development. BUILD is an amazing organization that changes the trajectory of high-school students from under-resourced communities, using entrepreneurship and experiential learning to do so. If you’ve met any of the 14-17 year olds that are part of the program, you’ve experienced firsthand how much you can help with just a little effort. If you haven’t, would love to see you get involved!

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Keith Cline is the founder of VentureFizz. Follow him on Twitter: @kcline6.

Jere Doyle is a Managing Director at Sigma Prime Ventures. He joined the firm in the fall of 2015, after spending time as an active member of the Boston startup scene, where he operated as either a mentor or seed / angel investor.  

Prior to becoming an investor, Jere founded Prospectiv, an online performance marketing services provider and operator of EverSave, a leading daily deals website. The company was acquired by Affinion Group in 2011.  

Keith Cline: Tell me about your background.

JD: My mom and dad were from Boston, but I was born in Europe and spent 12 years there, between Italy and England. We would come back to Massachusetts and go to the Cape every summer, so I think of myself as being from Cape Cod.

I didn’t come from a family of entrepreneurs. My dad was in the Navy at first and then he climbed the corporate ladder at a chemical company called Rohm and Haas. I have two brothers and a sister, who all decided to take more of the corporate journey.

I was different. As a kid, I was always dreaming of different business ideas. For example, down at the Cape one summer, I learned that a clock factory at the end of my road needed old newspapers to cushion shipments. They would pay a penny a pound. I went to a bunch of neighbors, collected their old newspapers, and sold them to the factory. I realized that the business would scale much faster if I had some help. I hired my brother and two of my friends. We scoured the whole town and we would collect between $5 and $20 worth of newspapers each time. I split the money between four of us. It taught me that you can take something that was earning a few nickels and dimes to building a team where it would expand and make considerably more money.

My dad went to Boston College. My brother and sister graduated from BC, too. During high school, my family was living outside of Philadelphia, so I applied to Penn State and thought I’d go there for college. But I ended up selecting BC. I guess it was the natural selection, as I always considered Boston as my true home. I had four great years there.

This led me to my next journey in business. The summer between my sophomore and junior year at BC, I went to Spain’s Canary Islands for a unique opportunity. Instead of my previous summer job of doing dishes on the Cape, I traveled abroad for a marketing job, where I helped to sell condos over there.

I had a very small apartment. I was all alone. I didn’t speak Spanish very well and I just remember it was really hot. I was homesick and wanted to quit and come back to the Cape shortly after arriving, but I felt like I had to at least stick it out for a week to give it a fair shot... then two weeks, then a month. As time went by, I got more used to it and ended up staying the whole summer there. It was life changing and taught me an important life lesson of perseverance and to never give up.

I was working for a marketing company that was working with real estate owners and developers who were looking to attract potential buyers for their condos. Our company was focused on customer acquisition, as we would book consumers for a vacation stay at a property. Then there would be the opportunity to pitch these potential buyers to either purchase a timeshare or they could buy a condo outright.

KC: What did you do right after graduation from BC?

JD: Not only did I end up working abroad for the same company the following summer, but I ended up working there full-time after I graduated from Boston College. I helped the company expand with offices in new locations like Sweden and Holland. 

After four years of traveling a ton and getting married, I decided to come back to the U.S. and attend Harvard Business School.  

After graduating, I originally accepted a job at General Mills. At this point, my wife and I had started building a family. I thought this would be my time to take a job in a large company and start climbing the corporate ladder. That’s when I got a call from my old boss. They wanted me to come back and run the company in Europe.

They had over-extended themselves by expanding outside of marketing and became an actual developer. The company was in really bad shape. I was fortunate to assemble a great team. We ended up turning things around and getting the company back to their core operations as a marketing organization. We sold it in 1998 and I stayed on for a year to fulfill my obligations.

KC:  Tell me the story about Prospectiv, the company you started.

JD: Afterward we sold the company abroad, I moved my family back to the U.S. It was 1999 and the internet 1.0 bubble was in full bloom. I started a new company called Prospectiv. We had a vision to help local retailers use the internet to drive people into their stores through coupons via email. The idea was fundamentally sound, but it didn’t work for SMBs. The internet was still too new and they didn’t know how to use it as a marketing tool yet. We ended up shifting to larger brands like TJMaxx, Staples, and Office Depot.

We raised about $11M through four rounds of funding. We were fortunate, as we raised our last round right before the markets plummeted in 2001. We stayed the course by working with a lot of retail and CPG companies and then moved over to to healthcare and pharmaceutical companies. We had a good run for four to five years. We were profitable, with 150 employees in Wakefield, and we paid all of our investors from our cash flow.

Then the recession of 2008 and 2009 hit. Companies started cutting their advertising budgets. We went from a very profitable company to one that was losing money so quickly. We had to make some hard decisions and lay off a bunch of people.

KC: Can you talk about the expansion with Eversave.com and an acquisition by Affinion Group for $30M?

JD: It was a dark time, but we noticed the rapid growth that companies like Groupon and LivingSocial were experiencing. They were doing coupons for local merchants, basically what we started out to do back in 1999. After talking to some merchants who were using these services, we got some great feedback. They loved the customer flow that deal sites like Groupon generated, but they hated the one and done! They didn’t know anything about the customer or how to get back in touch with them.

We already had the core customer acquisition DNA in place, which included a solid customer retention program for our big branded customers. So we decided to offer a new service to SMBs and called it Eversave. We offered daily deals in the form of coupons for merchants. But the key to our service was the backend. Our clients could keep in touch with their customers by offering a program of offers, not just one and done, through our triggered drip email system.

I went on to build Eversave while another executive ran Prospectiv’s core business. We grew quickly, launching in 25 cities with an inside sales team in Wakefield. Groupon and LivingSocial had raised massive amounts of money and were outspending us, but we were keeping pace with a fraction of the money. We were at a crossroads with the business and had to decide whether to raise capital or sell the business.

It was a hard decision, but it was good timing for a liquidity event for the management team and employees who had been with us for a long time. We sold to the Affinion Group in Connecticut, who had 7K employees and billions in sales.

KC: Do you have any interesting or fun stories to share from the web 1.0 bubble years?

JD: It was a crazy time, with lots of whacky stories. I remember we were on the west coast raising money and had been out there for over a week, literally criss-crossing all over the place. We were in San Diego and headed to LA for a meeting. On the way, we ran out of gas about 30 minutes from the meeting. I was with our CFO. We jumped out of the car and luckily found a gas station that loaned us a gas can. We got to the meeting on time, smelling like gas fumes, and somehow they still invested in the company. It was another lesson in perseverance.

KC: When did you start making angel investments?

JD: After I left the Affinion Group, I got introduced to Ty Danco. I’m not sure if he remembers, but we met at the Marriott in Cambridge in 2012. He took me around and showed me Dogpatch Labs and Techstars. Prospectiv was based in Wakefield, so I had no idea what was going on in the Boston tech scene and I was blown away. I didn’t even know what an angel investor was!

I started helping out a couple of entrepreneurs like Jebbit (founders from Boston College) and Rocketmiles. Since I have a lot of experience in customer acquisition, my skillset was of interest to companies who all needed help in that area.

A year later, I had invested in five to six companies and I was an angel investor. It was my passion for working with entrepreneurs that led me down this path and I realized this would be my next chapter.

I realized that it would be hard to keep up with the pace of writing $10K to $50K checks in startups five tp six times a year for the next 10 years, so I approached some mentors who were from the Cape about putting a fund together called the Oyster Angel Fund. Now that I had a few million dollars to invest, it became a full-time commitment. Over the next year and a half, I made 25 investments. I was enjoying every minute of it. I was helping entrepreneurs build out their teams, assist with the product roadmap, raising money, etc.

KC:  What were you guidelines for making angel investments?

JD:  I had three rules:

1. The company had to be in Boston, as I didn’t want to be flying around. I would only make an exception if I knew the founder well.

2. I had to love the founder / CEO and be able to help them and add value to the company beyond writing a check.

3. I had to both love and understand the space the company was trying to disrupt.

KC: Why did you join Sigma Prime?

JD: Sigma’s been around over 20 years. They have a great reputation for backing some great companies, and they’ve built a great firm. First, I really liked their focus. We primarily do Series A rounds, and I see a real opportunity here to build one of the top Series A firms on the East Coast. So many firms have either left for the West Coast, or shifted their focus to earlier seed stage rounds or later stage rounds. There’s a real vacuum at the Series A funding and Sigma is filling it.

I also like their approach. All of my partners here are operators. We’ve backed some great companies, and we get behind our entrepreneurs and back them for their entire journey. We understand it takes time to build great companies. Startups are hard, and it usually takes longer than expected. I like how my partners stick with companies. It matches with my belief in perseverance and it pays off. For example, Sigma is an early investor in both Interactions and CloudHealth. Both companies are on fire, both just completed large follow-on rounds of financing, and their revenue growth is through the roof.  But it wasn’t always that way.  

I was at a point last summer where I was thinking about a $20M to 25M Oyster Angel Fund II. Then the Sigma opportunity arose. They thought my experience in customer acquisition and as an operator would be a good fit for joining their investment team. Since we already knew each other well, we knew it would be a good fit. 

I’m one year into it and I’m enjoying it. We are committed to Boston and the entrepreneurial ecosystem here. We are building one of the leading Series A Venture funds here in the city. I can’t think of a better place to be.

KC: What stage of investments do you primarily target and what is the current fund that you are investing from?

JD: We focus on Series A investments on the East Coast, and we’ll do a few selective seed rounds in the fund, but not often. We are currently investing out of Fund 9, and we have some great companies in the portfolio. Many of the companies are under the radar, names you don’t read about every day, but the traction and revenue growth we are seeing is very exciting.  

KC: What sectors of technology, industries, or trends are of interest to you?

JD: Our interests are pretty wide, as we look at anything that is technology enabled. In our Fund 9, 19 of our 21 investments are SaaS businesses. They have solid CAC/LVT ratios, strong sales productivity and low churn. That’s what we look for. Other areas of interest includes AI, cloud, infrastructure, marketing tools, robotics, security, and storage.  

KC: What are the top traits you look for in terms of investing into a company or founder?

JD: I look for great entrepreneurs who can see an opportunity and not give up. A great leader who can run through the wall and get their team to run through the wall after them. Perseverance is key too, as the founder needs to be patient and deal with the ups and downs. And obviously a founder that has a vision to go after something big, that isn’t necessarily obvious.

On my own personal website I talk about the 5Ps, which are all key: Passion, Patience, Persistence, Principles, and Pride. You can have a big market and strong technology, but the success of a company all comes down to the people and the 5Ps.

KC: How has the Boston ecosystem evolved over the years?

JD: So much has changed in favor of the entrepreneurs. Incubators and angels didn’t always exist. If you think about it, the ability to start a company is a lot easier than it has been previously. There is so much help and access to mentors. It’s a great time to be an entrepreneur in Boston.  

KC: What companies in Boston, outside of your portfolio, do you find interesting?

JD: So many companies are doing well right now. Obviously companies like Wayfair, HubSpot, and Acquia are doing some great things and are successful.

Drizly is a company that I’m rooting for, especially since they are BC grads. Drizly was raising their angel round before I was an investor, so I missed out, which is a bummer!

KC: Who do you consider as your mentors?

JD: I’ve had lots of great mentors who were lot of the people who invested in the Oyster Fund. They are all really smart people, who have run successful businesses.

So many people have helped me along the way. I don’t even know where to start. Ty Danco has been great and I appreciate how he opened my eyes to the startup scene in Boston. Paul Flanagan and all my partners at Sigma have all been super helpful. And of course, my parents played a huge role in shaping who I am.

KC: Can you tell us about the Edmund H. Shea Jr. Center for Entrepreneurship Center at Boston College that you’ve helped launch?

JD: I graduated from Boston College in 1987 and at that point in time, no one was doing anything entrepreneurial on campus. As I got entrenched in the Boston ecosystem, I saw what was going on at the other schools and was very excited when BC asked me to help accelerate the entrepreneurship program on campus. I love being involved with my alma mater, and helping students learn about what it takes to start or work at a startup is something I really love.

KC: Outside of being a VC, what are you personal interests or activities?

JD: I have four kids: three girls and a boy, and I’ve been together with my wife since my BC days... over 30 years! So a lot of what I do outside of work revolves around my family. I love traveling, because you can learn so much from other cultures. I also love golf, mainly because of the relationships you can build out on the course. And I’m also a huge walker. That’s another reason why I love Boston. It’s a great walking city, where I walk from meeting to meeting.

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Keith Cline is the founder of VentureFizz. Follow him on Twitter: @kcline6.

MTV’s VMA Awards used to be one of my favorite programs to watch each year. Less pretentious than the Grammy Awards, it was the one time a year you could see artists perform with a little more edge. From Madonna’s iconic “Like a Virgin” performance to dozens of identical Slim Shadys walking the stage with Eminem, the night was historically about creating mic-dropping experiences that would leave fans talking for days afterwards.  If Sunday’s broadcast was any indication, somehow the VMAs seem to have lost their swagger.  Unless, of course, you are Beyoncé.

Beyoncé has created a larger than life persona, and has backed it up with discipline and hard work to ensure every performance outdoes that one before it.  She’s set a new bar -- repeatedly.  In short, she slays.

Are you a strong performer who aspires to slay every single day?  Check your game against these high performer bars.

1. Write Your Own Happy Ending.  Determine what success looks like to you and then work backwards, planning the steps you need to take in order to achieve that vision. Think about breaking it down into attainable, bite-size pieces.  It’s fairly challenging to accomplish big things if you don’t have a vision for what that ultimately is or how to get there.

2. Find a Role Model….and Then Become One.  Part of achieving your vision might mean you start to seek out examples of exceptional people that you admire and respect.  Learn what makes them so successful, then apply those lessons learned to your process, making them your own.  While imitation might be the sincerest form of flattery, being authentic and true to yourself is even more impressive.

3. Step Out of the Comfort Zone.  We all have certain things we are good at – naturally or through hard work – that quickly become the things we’re known for.   Capitalize on these – and then push past your established comfort zone. Enter the “stretch” zone.  We create impact when we follow our passions, take risks, and continuing evolving.  No one thrives by resting on their laurels.

4. Bring Others Along.  Whether it’s for moral support, collaboration, or just simply to make the journey a little more fun, creating a trusted posse is a vital step.  While you might be an exceptional individual contributor, you know you’re ready for the big stage when you are able to influence and inspire others.  Find those people and nurture those relationships.  

5. Never, Ever Give Up.  No matter how talented you are, you can’t achieve exceptional results the first time out.  Set a goal, plot a roadmap to get there, and be prepared to dust yourself off and try again until you nail it.  With an open mind, you’ll learn along the way, and perhaps end up with a better outcome than you originally set out for.

By applying the steps above, you might just find yourself slaying in your own job.  Go be legendary.

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Christina Luconi is Chief People Officer for Rapid7. Follow her on Twitter: @peopleinnovator.

Image via Google Images

Woody Benson has witnessed a long standing career in the tech industry across multiple operating and executive positions. He's seen a high level of success as an investor too with several exits including LogMeIn, where he is still on the Board of Directors. He saw LogMeIn go public back in 2009 and recently merge with Citrix's GoTo family of products. Benson recently joined LaunchCapital as a Venture Partner, where he is focused on early stage investing. Read more in the interview below.

Keith Cline:  Tell us about your background.

Woody Benson:  I grew up in Swampscott Mass. I am the youngest of three boys and my father was an accountant at a Big 8 firm, having started by taking accounting classes upon return of the World War II. He graduated from Bentley College in 1948 from night classes in the Boston location, where the great Harry Bentley actually taught some of the classes.

I was a regular North Shore sports focused kid playing football, street hockey, stick ball, little league, and the whole bit through the Bobby Orr/Big Bad Bruins hockey explosion years. We lived on a hill by Fisherman’s Beach in Swampscott, where I hung out with the local commercial fisherman and I worked on lobster and commercial fishing boats with my friends.

At 14 years old, I wanted to start a lobster business and I did. I borrowed money from my father (and created a bank book and paid him back weekly till fully paid) and bought a boat and 25 lobster traps. Everything was going fine until a major hurricane hit and I lost most of my traps. I said, no problem. I’ll going to start a water taxi business (my first pivot).

I became a boarding student to Governor Dummer Academy (now known as The Governor's Academy) as a freshman. I spent most of my four years at GDA on probation or in trouble. I was not a good student at all, until I met some great teachers who saw something in me that no one else saw.

I have always loved business and my father, who came from nothing and had sent his children to private schools, said I should learn how the guts of business worked. I applied to Bentley and Boston College. I was accepted to Bentley, I am sure as a legacy. It sure wasn’t my grades.

During my years at Bentley, I worked full time bartending and waiting on tables. I really learned how to sell, multi-task, use customer facing psychology and almost took a job at Berringer Wine as their National Sales Manager. But I was dating a girl who was a computer science major and was working part-time at an accounting software company, making $40K a year and driving a brand new blue Celica. I had to me get some of that.

My brother had told me that there were three industries going to take off in the 80s: micro-computers, solar energy, and cable TV. In November 1980, I started selling computers at Computer City store in Charlestown for $140 a week, plus commission. It was a crazy time to be in that business as we became a top Apple reseller in the country and people like Mitch Kapor, Bob Frankston, Adam Greene, George Tate often came by, even Steve Jobs.

Somehow I grew from the backroom of a small Computer City store to an assistant manager in a satellite store. A year later, I found myself in the corporate offices. A year after that, I helped oversee the liquidation of our inventory, as the company went bankrupt. Computer City died through a combination of full page ads in the Boston Globe, and zero supply chain or regard for planning. Fun times.

KC:  How did you get into the tech industry? Can you share the different roles and companies you worked for?

WB:  After Computer City, I worked in the top manufactures rep firm in New England (every major vendor in the nascent personal computer world went to market using rep firms, including Apple). Since our firm actually did represent Apple, if you were a manufacturer you had to go through our company. From 1982 to 1987, I represented some of the largest vendors like Sony Monitors, Sony Recording Media, Hayden, Software Publishing, Great Plains Software, and many more. We set up distribution for these vendors in the six New England states and sold to computer retailers, mass merchants, wholesale clubs, distributors, direct mail companies and OEMs. I lived through six years of every day being a product launch for somebody. Lessons, money, and opportunity abounded.

From there, I was recruited into Lotus Development, at that time the world’s largest software maker, to create a global channel OEM strategy. We sold tens of millions of Lotus Works’ software to all the leading OEMs like Packard Bell, IBM, NEC, HP, and more. And we got to bring Leon Navickas’ piece of balsa wood to market. The embedded version of 1-2-3 into an HP calculator spawned a business that Palm eventually purchased.

Jim Manzi called me one day and said that Andy Grove (the Intel CEO) told him that networking was going to be a big thing and I should go work in a new group called to spearhead our networking efforts. This did not last long, as I got a call from Shiva Corp which was a Kendall Square start-up funded by Kleiner Perkins & Greylock. They needed someone to run sales and marketing. So I left my job at Lotus, where, at that time, I was working for the CEO and had all that security: big pay (at the time) and a first class lifestyle (we called it the 18” shrimp days). I went to work for a startup that was essentially broke, had so many lawsuits against it (Christmas parties gone wild and an employee orientation that can’t be described). I did it because I saw a product in their lab called the LanRover that I felt was huge. We built LanRover Inc and Shiva from a small Apple networking company into a major player in the space, grew sales to almost $300M per year and went public in 1994.

I started at Shiva in 1992 and worked in Kendall Square and re-built the sales/marketing team. I helped plant that flag into every country around the world and almost died in Japan from chicken pox. We set up an awesome distribution system that included competing OEMs (IBM, HP, Motorolla, etc), global distributors and sophisticated two step distribution. We left Cambridge for a campus setting in Bedford. We almost merged with Ascend Communications, who later sold to Lucent for $20B with a B$$.

Toward the end at Shiva, I got a call from a recruiter who represented Summit Partners (a large Boston PE firm), who had an investment in a Calgary company called MCK Communications. It did what Shiva did, but for voice. So in April 1997, I became CEO of MCK Communications. Quickly, we revamped our products, signed OEMs, moved to Boston, and invented a new branch product and established a unit to market to CLECs (new telephone companies offering services).

I replaced the entire management team and built a new team. We were able to grow that business rapidly and go pubic on my birthday in October 1997. With a peak market cap of close to $1B, MCK was a big win for our investors, Summit & Lazard Technology Partners. In 2000, I became Chairman of MCK and tried to take some time off with my family. We had a nice house, I had some money, and a CV. But I fundamentally knew that my greatest assets were the people I knew, who knew me, and that I was hopelessly in love with what was next.

KC:  Why did you end up becoming a venture capitalist?

WB:  Taking MCK public, flying around the world looking for public shareholders in private jets, meeting real bankers, I realized as great as I was being a CEO. I fell in love with the idea of being on the other side of the desk.

I started the Boston office for Lazard in September 2001. I always wanted to be a VC. A friend of mine back from the rep days, Stu Singer (a great mentor), told me he was doing some diligence work for Greylock and he explained to me how the VC business worked. So, when I interviewed with the great Henry McHance (Greylock founder) for the role at Shiva, I told him that I wanted to run a sales/marketing function for a VC-backed company and make them money, then be a CEO of a VC-backed company and make them money, and then be a VC. So I guess I was sort of self-programmed from a career perspective.

KC:  Can you share some of the investments that you made while at Lazard Technology Partners and Prism VentureWorks?

WB:  At Lazard, I invested in Tazz Networks, Kubi Software, and Aptsoft. Of those three, Aptsoft was sold to IBM. The others, while great ideas and teams, did not work out. At Prism, I invested in LogMeIn, M:Metrics, Maven Networks, KickApps, 5:1. Each of these companies had an exit, but m:metrics, Maven, and LogMeIn were the best. Some that didn’t make it were Everypoint, Comedy.com, and Worldwide Biggies.

KC:  You were an early investor in LogMeIn and remain on their Board of Directors.  What was it about the company that led you to make an investment in the early days?

WB:  When I saw LogMeIn, it hit me like a ton of bricks that remote access as a service was a killer idea. The exact feeling I had when I first saw Shiva and MCK. It was a no brainer. Other people had issues with the deal, but not me. Also, they had a great business model, which enabled them to invent the freeium business model. Mike Simon was an awesome exec and the tech co-founder, Marton Anka, was as smart and talented as you could find.

I was lucky to have found the company and fortunate to meet so many great people and become close to so many Hungarians, too. When I met LogMeIn they were located in Budapest and that’s where the development still takes place. In many way, this is the VC dream: Be the first A round investor, lead the company through private financing and to an IPO, complete a secondary, and then do some kind of blockbuster deal which we just announced with buying the Citrix GoTo business.

KC:  You recently joined LaunchCapital as a Venture Partner.  What prompted you to join the team there?

WB:  I have worked with Elon Boms for several years across a few projects with ArccosGolf being the better known deal. I have great respect with what he, the Launch team, and the Pritsker family office are trying to accomplish. So when he approached me about being a Venture Partner, it was a complete no brainer.

In the venture business, it's best to do business with people you know and trust. Venture is hard and I was once told, “The worst ship to have in heavy seas is a partnership.” Also, Launch is not a fund, so there's no fund economics and portfolio-based decision making (which is a very good thing and LPs who don’t see that are missing something). And my mandate is to do early deals, which I really love. I am not a financial engineer and I love working with young and early teams and always searching for what the next new thing is.

KC:  You have been an investor in the Boston tech scene since 2001, how has the ecosystem evolved since then?

WB:  Oh man, I don’t know where to start. In 1980, there was a small ecosystem in the Boston Computing Society, that’s about it. But now, with incubators, MassChallenge, angel investors, universities, and hundreds of companies started from veterans of other companies, I would say our eco-system is world class.

I laugh at all the Valley comparisons. Tet them be great, they are. And so are we. I am very proud of the GE move to Boston, it says a lot.

The fund raising side has changed so much. Lets start with the end of the formal A round. It takes less capital to start a company now, and entrepreneurs have access to friends and family to get started, so there really is no traditional A round anymore. That quickly evolved, and there are less firms doing A round deals anymore. Firms like Kodiak, NorthBridge, Prism, etc. did not evolve into something else and the LPs like super specialized VC firms. This, combined with the increase of angel investing based on the wealth created by tech vets, has meant that companies can go one to four rounds without talking to a VC. And syndicate angel networks like AngelList further change the dynamic. Not to mention that some companies can crowdsource their way through the cycle.

KC:  What stage of investments do you primarily target?

WB:  We are not a fund, more like a balance sheet. We like early deals with big markets and can go deep on some. But our sweet spot is post-friends and family and to be involved in the first seed round.

KC:  What are the top traits you look for in terms of investing into a company or founder?

WB:  Vision, integrity, and humality. A leader who can attract others. A sense of humor is good too.

KC:  What sectors of technology, industries, or trends are of interest to you?

WB:  Right now, AI, bits, machine learning, analytics, sports tech.

KC:  What companies in Boston, outside of your portfolio, do you find interesting?

WB:  I am in awe of the biotech and life science companies. I think the AI and robotic trend is really interesting. I think these all show our university roots and I find these next gen technologies really interesting.

KC:  Greatest misses? What company(ies) have you passed on that you wish you hadn’t?

WB:  I’ve missed on a few that have had great financial returns, but I look at each deal as a mini-marriage. A five year deal where you spend a lot of time together, need to identify problems together and create solutions. From that perspective, I have no regrets about passing on any deals.

KC:  Who do you admire or who has been the greatest mentor for you?

WB:  I’m so lucky here. There are the ones from Governor Dummer I mentioned, but Jim Keily from Bentley let me be the first student in his Business Communication program, which earned me an internship in advertising. In the early days, Marvin Grossman and Stuart Singer were key. They taught me the psychology of selling to and working with retailers and how to get them how to behave.

At Lotus, Jim Manzi and Frank Ingari were big mentors and supporters. From Jim, I learned how to think, act, and play long term strategic ball. At Shiva, John Doerr and Henry McHance were huge supporters and mentors. I was lucky to spend a lot of time with John on pricing strategy which I will always appreciate. And at an industry conference John, my wife, Beth, and I were in the kids center cutting paper out for our then-two year olds and I got to see John as a person.

At MCK, I got to learn from Greg Avis, a Summit co-founder and all around super star. At MCK/Lazard, one of the original gentlemen of VC, Russell Planitzer, took me under his wing and taught me the VC business. My mentors have been a blessing me and I try to mentor others and would encourage everyone to find mentors or mentees. In fact one friend of mine, Colin Mahoney (Vertica/HP), has a reverse mentor dinner where he invites his mentors out. Imagine Andy Palmer, Howard Anderson, Chris Lynch, and me at a table. 

KC:  Outside of being a VC, what are you personal interests or activities?

WB:  I am married (now for 28 years) and love spending time with my family. We just moved into the Seaport, so we're exploring and dining a lot in the area, which is fun. I love sports, so we watch a lot of the Boston teams. I also love to play golf, which is mostly done on the Cape at New Seabury all 12 months of the year with the first tee times. And we loving boating around the Cape and Islands.

KC:  What type of music do you like?  

WB:  I'm about to see Government Mule, Umphrey McGee, ZZ Top with Greg Allman, and TTB. But no doubt my favorite is Frank Zappa. After 100 produced albums, thousands of live shows, and a vault which is getting published, there is always something great to listen to.

KC:  Are you involved in any charitable organizations?

WB:  I am an executive in residence at Bentley and teach an MBA class there called corporate immersion, where we won an international award and that program is now a graduate school requirement. Aside from financial donations, it's my way of giving back. I have been involved with the Red Cross and Dream Big!, as well.

 

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Keith Cline is the founder of VentureFizz. Follow him on Twitter: @kcline6.

I’ve had a number of conversations recently with people about “having it all.”

It’s long been debated whether or not this whole notion is a myth or if it’s actually achievable. Certainly, there are a fair number of us trying to cram a whole lot of life and achievement into our already jam-packed existence and trying to make it reality. But the question remains: Can we actually be successful?  

I’m not entirely sure of its origin, but I think the whole notion of “having it all” started with a book written by Cosmopolitan Magazine founder Helen Gurley Brown. A true thought leader, she added a bit of glamour and solidarity for women living their hard-fought lives as single, independent people. And yet, I’m going to take a wild guess that when she penned her book, Having it All in 1982, she didn’t intend for it to mean “Having it All… at the Same Time.”

The book was written as a roadmap for creating your own destiny, which was a truly novel concept at the time for women. Over the past 25 years, we’ve seen an increasing number of female leaders step up to talk about how they’ve created their own paths, what works for them, and how to stand tall in the face of adversity.

Still, perhaps a refresher course for all of us might be a wise idea in today’s world. Whether you are a woman or a man, understanding what path you are on and having some sort of guide to get there is not just smart—it might just be good for your sanity.

Let me get a little personal to make my point.

I’m a single mother of two teenage daughters. I also have a career I love and people in my life I care about. Any problem I have is strictly first world. I have plenty to eat and a roof over my head. My struggles come in the form of wishing I had a night off sometimes to enjoy dinner with a friend or trying to figure out when I will find the time to get an overdue oil change for my car.

In essence, I have a pretty good life. And yet… I want more. I want the proverbial “all.”

WHAT DOES 'HAVING IT ALL' REALLY ENTAIL?

“All” is defined differently for everyone trying to achieve it.

While I won’t turn this into a feminist rant, I do believe that women are held to a different set of expectations than men, at least (very) generally speaking. We are the ones who give birth. So of course, in modern society, we tell women they can have a family and a career. While some companies have moved toward adding mothers’ rooms and have paid maternity leave, neither benefits are close to universal.

But then what? Plainly, I’d argue that as a society, we are a long way away from enabling women to have a thriving career and family at the same time.  

Several years ago, a young woman early in her career told me about her aspirations. “In the next five years, I want your job,” she said. “And I’d like to have started a family. And I’d like to only work three to four days a week.”

Um, yeah. That sounds awesome. However, she was none-too-pleased when I offered a dose of reality. "Yes, absolutely you can achieve that," I told her. "But perhaps you just need to adjust your expectations on time frame and/or the order in which you plan to achieve these goals."

The reality is, sure, anyone can have kids. Anyone can build an incredible career. I’m a firm believer that you can do just about anything you set your mind to and efforts on.  

I’m also a firm believer in reality. In this young woman's case, yes, she can start a family and elect to ease back on hours to commit more time at home. There are a number of companies and jobs that support just that and I applaud them. She can also focus on her career, climbing the ladder to a serious leadership position. However, doing all of this at exactly the same time is not just a recipe going crazy—it’s a fast path to failure.  

FORGE A PATH WITH YOUR SANITY INTACT

Man or woman, we all want to achieve. So how do we create a sane path for ourselves? Here are three quick reality check questions to ask yourself before you get started. 

1. I work smart and efficiently. True or False? Building a fantastic career doesn’t always mean you need to be the first one in and the last one out. However, it does mean you have to make the most of your hours. Be present during the core hours for meetings, and find creative ways to maximize your time at work. Stay focused, skip the twice-a-day runs to Starbucks, and you’ll likely gain some precious time back in your calendar.

2. I spend quality time with my kids/family/friends. True or False? There is a myth that to rise up at work, you’ll have to forego time spent investing in your personal relationships. But really, it’s about making the most of the time you have with any of these loved ones. Choosing to come in early so you can maximize family time at night, or refusing to even look at a computer screen for work on a Saturday are choices that you are in control of. Carving out the time, keeping it sacred, and then being present when you have it are all keys to maximizing quality time with loved ones.

3. I have a clear idea of what I view as 'success' in my life. True or False? It’s easy to feel like you aren’t doing anything particularly well if you don’t have a vision for yourself of what you’re actually trying to achieve. Take the time to figure out what defines success for YOU (not for your mom, or your boss, or anyone else whose opinion you might value—this is about YOU.) Then work backwards to craft a plan to get there. As you do this, apply rational timeframes, experiences that work for your lifestyle, etc.  

With a little dose of reality and some thoughtful planning—maybe even a bit of sense of humor—you can have it all.

It just might not be all at the same time.

 

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Christina Luconi is Chief People Officer for Rapid7. Follow her on Twitter: @peopleinnovator.

Image via Shutterstock 

If you think of the top Boston-area colleges and universities that consistently churn out entrepreneurs year after year, Harvard, MIT, Northeastern, and Babson probably come to mind.

You might not think of Boston College.

BC’s Carroll School of Management—which was ranked the third best undergraduate business school in the country this year by Bloomberg—is highly regarded for producing successful investment bankers and consultants. But it isn’t as well-known for spawning tech startups.

“BC has been doing a little bit in entrepreneurship for a long time,” said Jere Doyle, the executive director of BC’s new Shea Center for Entrepreneurship and managing director at Sigma Prime Ventures in Boston. “But over the past decade, there’s really been this push by students, faculty, and alumni to get more students involved with startup companies.”

Following a generous gift from the family of the late entrepreneur and VC, Edmund H. Shea, Jr., BC launched the Shea Center for Entrepreneurship last September. Previously, there was not a lot of institutional support for students interested in entrepreneurship at the university. The formalization of the Shea Center has taken that to the next level.

Together with Kelsey Kinton, the assistant director of the Shea Center, Doyle is giving BC students the resources and mentorship needed to start or join a company. Their goal is not for students to create ventures at BC—but rather for students to be what they described as “startup ready.”

“We have the perfect type of students to go on and work at a startup or be a co-founder,” Kinton said. “We recognize that we’re not going to be producing hundreds of companies each year. But we want students to learn what entrepreneurship is, and learn to think like an entrepreneur. That mindset can allow you to be disruptive in any industry after graduation.”

Armed with a new hub on campus and a group of passionate alumni, BC is getting more students interested in joining startup companies than ever before. The Shea Center has put BC on the map in terms of entrepreneurship—and it’s out to prove that startups aren’t just Harvard and MIT’s game.

BORN OUT OF BC

Nick Rellas reached for a beer in his dorm room at BC only only to find an empty fridge.

He sent his friend and former classmate Justin Robinson a text, asking why he couldn’t get alcohol delivered from his smartphone. The two stayed up all night researching, and determined that alcohol delivery was perfectly legal—just nobody had done it correctly.

Soon the idea for Drizly was born. The on-demand alcohol delivery service officially launched in Boston in 2013, and has since expanded to 23 different markets across the country. Drizly has raised $32.8M over the past four years, including a $15M Series B round of financing announced earlier this month.

Rellas and Robinson graduated from BC in 2011 and 2012, respectively. Both attributed much of their success to their time and formation at BC, including support from professors. But they added that there was not much infrastructure or institutional support at the time to help launch Drizly.

“It seemed like we were way behind what other universities were doing, which was frustrating,” Robinson said. “There really wasn’t a path for us to follow, but we made the most of it given the resources we had.”

Drizly is part of a recent wave of startups that have emerged out of BC. Over the past five years, startups launched by recent BC grads have received over $100M in funding. Many have participated in elite accelerator programs, including Y-combinator, TechStars, MassChallenge, and Summer@Highland.  

Companies like WePay, Jebbit, NBD Nano, Wymsee, LocalOn, and Streak Media all have ties to the university. The founders of Jebbit, Drizly, and NBD Nano were also named to the Forbes “30 under 30” List in 2015.

“When Bill and I were at BC, there certainly wasn’t an infrastructure or network for entrepreneurs,” said Rich Aberman, BC ‘07 and co-founder of WePay. “Now that’s changing.”

1-STOP SHOP FOR ENTREPRENEURSHIP

The Shea Center has quickly become the university-wide focal point for entrepreneurship at BC over the past year.

Doyle and Kinton are working to get students of all majors across the university involved with their programs. That includes working with students with business ideas, teaching them what it takes to produce a business plan, and most of all, teaching them what it's like to work at a startup.

“For the most part, 22 year olds are not ready to start their own companies,” Doyle said. “I went and worked for a startup after I graduated from BC, but that was very unusual at the time and I had no formal training. So we want to make sure our students are startup ready.”

The Shea Center currently offers a variety of programs and resources for students interested in learning about entrepreneurship—from educational to experiential training. It recently created an  entrepreneurship co-concentration within the Carroll School of Management, which includes a cluster of classes dedicated to learning about the fundamentals of non-traditional business.  

The Center offers a number of co-curricular programs, including a speaker series, female founders’ day, and weekly lunches with an entrepreneur. It has also partnered with BC’s popular Tech Trek programs, which introduce students to tech executives, entrepreneurs and VCs in San Francisco, Silicon Valley, Seattle, Boston, New York, and Ghana. The Shea Center also hosts a startup fair in the spring, which brought in 35 different companies offering internships and full-time positions this past year.  

“The launch of the Center has helped put us on the map in terms of our external audience as well,” Kinton said. “So when startups want to come recruit for their businesses, BC is a great place to start.”

WePay CEO and co-founder Bill Clerico formed the Boston College Venture Competition (BCVC) during his senior year in 2007, hoping to create a like-minded community of students interested in entrepreneurship. The competition has quickly grown in popularity, and now offers grand prizes of $10K to both its for-profit and social enterprise competitions.

“Entrepreneurship at BC has really accelerated over the past seven to 10 years,” said Peter Bell, a BC trustee and senior advisor at Highland Capital Partners. “The WePay guys really started a movement when they decided to form the venture competition as students.”

The Shea Center also hosts an annual elevator pitch competition, and it launched a six- week accelerator program this past year. Additionally, the Center launched its Internship Program this summer, which gave 25 students a $1K stipend to get hands-on experience at a startup.

“A lot of startups can’t afford to pay students,” Kinton said. “We realize this is such a valuable experience to be working at these small companies and contributing to a team, so we wanted to give students a stipend to get real experience in the startup world.”

A PASSIONATE ALUMNI NETWORK

Doyle hopes the Shea Center can impact all 9K of BC’s undergrads in some capacity during their time at the university. Part of that effort includes bringing more BC alumni back to campus to share the stories and lessons they’ve learned as entrepreneurs.

“Part of what makes BC special is the alumni network, and the fact that so many alums want to help other alums out,” Bell said.

Bell has worked closely with the WePay team over the past several years, both as an investor and board member. He also co-founded the BC Tech & Entrepreneurship Council in 2001. It is one of the biggest and most impactful organizations building bridges between BC undergrads and the alumni community.

Bell is accompanied by other prominent investors from various VC firms on the council, including Highland Capital Partners, Spark Capital, Sequoia Capital, Shea Ventures, and Flare Capital Partners. Many are plugged into the BC startup ecosystem, and regularly support companies born out of the university. For example, Jebbit CEO Tom Coburn co-founded the Soaring Startup Circle (SSC) two years ago, which is a rotating accelerator program specifically designed to help BC students take their businesses to new heights. The SSC provides office space, experience, and networks for a few BC teams during the summer.

BC is different from many other local colleges and universities in the fact it does not have an engineering school. BC is a Jesuit, Catholic university that prides itself on its liberal arts curriculum—and many alumni are grateful for that.

“I’ve truly seen BC’s motto of ‘Ever to Excel’ and the Jesuit motto of being ‘Men and Women for Others’ play out in the startup world,” said Pat Grady, BC ‘04. “If you’re going to do something, you do it right. And I’ve seen that in the culture of the types of people who succeed in startups.”

Grady is a partner at Sequoia Capital in San Francisco. Out of Sequoia’s team of 30 investors, four are BC grads. That’s not a coincidence.

“I’ve been able to plug a BC grad into any role and see them succeed,” he said. “Now more and more people are thinking about joining startups after school. As alums, we’re here to help with that.”

 

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Bennet Johnson is the Digital Marketing Intern for VentureFizz. Follow him on Twitter: @bennet_15

All photos courtesy of The Heights

The first social networking site on the internet came out of Boston—and it wasn’t Facebook.

PlanetAll was founded in 1996 by Warren Adams and Brian Robertson. Before the term “social networking” existed, the duo out of Harvard Business School and MIT wanted to create a way for users to connect and stay in touch with different groups after college. Sound familiar?

Once touted as, “The only address book you’ll ever need,” PlanetAll had many features similar to Facebook—and let users set up web address books, calendars, and reminders to stay in contact with others. The site had over 100K different interest groups on its platform, and offered an innovative feature that would notify users when they would cross paths with their contacts.

At the time, PlanetAll was one of the largest and fastest growing databases on the web—adding nearly 20K users a day. The site had 1.5M members when it was sold to Amazon for $100M in 1998, and it secured a patent two years later for a “Social Networking System.”

“In two short years, we built the first social networking company,” Adams said. “In the internet business, we didn’t know if we would be dead one day or hit a homerun. And we felt like we had made it.”

We wanted to take a look back 20 years ago, and uncover the story of how the first social networking site was built right here in our backyard.

I recently spoke with Adams about his idea for PlanetAll, how he raised millions from local investors in the late ’90s, and how he dreamed of creating an online database that connected everyone in the world.

He was just eight years too early.

A WAY FOR COLLEGE FRIENDS TO STAY IN TOUCH

Before graduating from Colgate University in 1988, Adams wanted to create a database to keep in contact with his college friends during the summer. He essentially wanted an address book that detailed where his friends were going to be, and if they’d cross paths at any point in the future.

With the growth of the internet in the mid-’90s, Adams had the perfect chance to turn his idea into reality.

After graduating from HBS in 1995, Adams passed up a career in consulting to start PlanetAll. He didn’t have a technology background, so he teamed up with Robertson, a 22-year-old tech whiz out of MIT and former Canadian national barefoot water-skiing champion.

“Our idea was pretty simple,” Adams said. “You just needed to have the marketing and technology to get more and more users on the database.”

The duo started developing the site based out of a windowless office in Kendall Square. Robertson recruited 12 of his tech-savvy fraternity brothers to do programming to launch the site. Similarly, Adams also reached out to some of his HBS classmates to help with the initial business plan.

The company survived on money from its founders and a number of angel investors. Adams and Robertson quickly raised $1M within within six months of launching the site. In June 1997, PlanetAll raised a $4M round led by CMGI @Ventures, a local VC firm that invested in internet companies.   

The team’s objective was simple: Get big fast. They launched planetall.com in the fall of ’96, convinced that being the first of its kind on the web would ensure success.

THE FIRST ‘WAVE’ OF SOCIAL NETWORKING

PlanetAll was not the only company experimenting with this technology at the time.

SixDegrees launched in 1997 out of New York City, and was based on a “social-circles network model.” It allowed users to list friends, family members, and other acquaintances both on the site and externally. SixDegrees had nearly 3.5M members, and was eventually purchased by YouthStream Media Networks for $125M in 1999.

“We were really part of this first wave of social networking,” Adams said. “For a while, we were the only two players. We both got acquired at the same time.”

Social networking started to hit its stride with Friendster in 2002. Friendster, MySpace, Plaxo, and nearly 10 other sites enjoyed brief success in this second wave of sites, but they ultimately failed to generate enough users. Adams explained that the third wave won the web when Facebook and LinkedIn entered the scene in 2003 and 2004.

“That was our dream,” he said. “It certainly didn’t have to do with the idea, since the idea was out there over a decade before. It had to do with the technology available, bandwidth, and getting everyone on the same database.”

A SHIFT TO ECOMMERCE

Amazon founder and CEO Jeff Bezos was so intrigued by the concept of PlanetAll that he bought the company for $100M in 1998.

"PlanetAll is the most innovative use of the Internet I've seen," Bezos said at the time of the buyout. “I believe PlanetAll will prove to be one of the most important online applications."

After initially saying the company would remain in Boston, Bezos decided to ship PlanetAll out west. Adams and Robertson moved to Seattle, and both became executives at the online giant.

At the time, PlanetAll had 1.5 million users and was growing faster than the internet. But for whatever reason, Bezos decided not to pursue social networking.

Within two years, Amazon had shut down the PlanetAll site, and many users were upset. One journalist even said she was “in mourning” for the service.

“Amazon took us into using social networking for e-commerce,” Adams said. “Bezos and his team had this brilliant vision for an online bookstore. He asked, ‘Would you buy more of a book if X person read it and loved it?’”

Amazon converted many of PlanetAll’s features into eCommerce, which became very lucrative for the company. Amazon’s “Purchase Circles” tool was based on PlanetAll, and some of its code was used to improve Amazon’s Friends and Favorites technology. Adams also pioneered “Amazon Anywhere,” which allowed users to shop anytime on their mobile devices. Robertson went on to create Amazon’s toy store. To this day, Amazon holds a U.S. patent on social networking based on PlanetAll.

LEAVING A LEGACY

After two years at Amazon, Adams left the company in 2000. He moved back east to start a family and fulfill a lifelong dream of living full-time on Martha’s Vineyard. Adams turned his professional attention to advising and investing in early-stage companies through his find, Vineyard Ventures.

After traveling in Patagonia, Adams was motivated by the region’s beauty to create one of the first for-profit conservation funds. He established Patagonia Sur in 2007, which acquires, conserves, and preserves large tracts of land in the region. The $25M fund has a number of Chilean and American investors, and has accumulated 700K acres of land over the past decade.

Robertson also left Amazon in 1999 and went on to have a remarkable career as a pioneer in the solar field. He was an ambitious entrepreneur—always ready to take on the next challenge. Robertson created Visible Markets, the first electronic trading platform for the U.S. bond market. He also graduated from HBS and co-founded Sun Edison LLC, North America's largest solar energy services provider, which was acquired by MEMC Electronic Materials for $200M. Robertson also served as CEO of Amonix, which became the largest manufacturer of concentrated photovoltaic commercial solar power systems during his tenure.

Robertson tragically passed away in an airplane crash in 2011. He was just 38 years old, and left behind a wife and three children.

“Brian was remarkably influential in solar financing, solar energy, and social networking,” Adams said. “He got things moving that changed the world, and he’s incredibly missed by so many.”

Adams is currently a fellow at Harvard’s Advanced Leadership Initiative. He’s learning to combat climate change, tackling the issue from a for-profit perspective. Looking forward, he wants to help create ventures that make a difference in the world.

It’s been 20 years since Adams and Robertson started PlanetAll. Their idea may have been a bit before its time, but the impact they’ve had on social networking, as well as for-profit conservation and solar energy, will endure for years to come.

“We built one of the largest and fastest growing databases on the internet,” Adams said. “We didn’t just want to dream about the future—we wanted to create something that would change the world.”

 

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Bennet Johnson is the Digital Marketing Intern for VentureFizz. Follow him on Twitter: @bennet_15

I consider myself a builder. To do this, one of the keys is realizing I don’t always have all the answers. Rather, I rely heavily on asking one very simple question: Why? It’s likely the single most important word in my vocabulary. 

Often in business — and in life — people are not comfortable challenging others (and sometimes even themselves). Asking questions about why something is the way it is or why it’s done a certain way can come off as judgmental and antagonistic. It’s also possible that whoever you’re directing the questions to may feel defensive or insecure. 

I suggest that asking why should be seen as quite the opposite. 

WHY 'WHY?' IS SO IMPORTANT

When we start asking questions, we are seeking to learn. We are looking for the true reasons behind something, which allows us to gain knowledge before we attempt to offer new ideas. Rather than be seen as a form of disagreement, it can be an exceptionally powerful and productive method for evolving an idea. 

Why is this so important? Change is necessary for evolution. When we start asking why, we’re able to determine if we’re on the right track or we’re able to push the boundaries further and explore more deeply before we make decisions. 

It also allows us to think more analytically. Have you even invested in an idea or process and supported that investment with time, effort, and money? We often keep moving forward and don’t stop along the way to invite others to evolve our thinking or approach — even when we might need an outside perspective or have been stuck on the same problem for an extended period of time. When people are involved and start asking why, it allows us to pause and reflect on whether we are creating the best possible solution. 

In my role, I am constantly in the position of creating and finding solutions to new problems. I might have a decent initial idea about how to solve something, but I invite others — early and often — to provide me feedback and challenge my thinking. While I don’t always agree with everything that surfaces, the why questions and collaboration that follow never fail to push the results to a better place than if I had gone it alone. 

Have you ever been in a meeting where you’re sitting and listen passively to someone droning on about XYZ, and feel uncomfortable asking why?  Maybe you fear looking foolish, because you think you should know the answer. Or maybe you are concerned you will offend someone. Or even still, maybe you just don’t think it’s worth the effort.  

I challenge you to rethink your silence. 

HOW TO START ASKING WHY

By asking questions, you fill in the gaps of your own understanding and potentially others in the room who face the same dilemma. Rather than assuming you understand the intent and potentially creating gaps in alignment, you fill in the missing pieces with the right information. Once you get to the core of the issue, you can focus on the right problem.  

Aren’t sure if you are ready to raise your hand publicly and start asking this powerful word? Try this simple exercise by yourself today:

1. Pick a problem you are facing — any problem.

2. Ask yourself why it’s happening.

3. Ponder the answer. Then ask why again.  

4. Rinse and repeat at least three times.

If you are really seeking true understanding, you’ll likely come up with an entirely different answer than you originally anticipated by participating in this exercise.  You’ll find yourself with a fresh perspective and a new path to innovation. Give it a try. Then go bigger and attempt it with others. 

Want to instantly feel more empowered and innovative? Rather than being intimidated by the notion of why as a form of disagreement or challenge, embrace it as a power word. You might just find yourself — and your team — with a far better outcome. 

 

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Christina Luconi is Chief People Officer for Rapid7. Follow her on Twitter: @peopleinnovator.

Image via Unsplash