Clearsurance: The First-to-Market Crowdsourced Community for Insurance Ratings and Reviews

March 1, 2018

Clearsurance: The First-to-Market Crowdsourced Community for Insurance Ratings and Reviews

“From an early age,” Clearsurance Co-Founder and CEO Michael Crowe said, “my father really drilled into me that your career goal should be to work for yourself—to be your own boss so you're not at the mercy of something you have no ownership in.”

This advice would become the basis for Crowe’s professional life from the very beginning, when he, like a number of entrepreneurs, went to Merrimack College. But rather than going a more traditional business route with his studies, he used his time as an undergrad to study political science and government. This was because, originally, he planned on going to law school.

“I didn't have a clear sense of exactly what I wanted to do at the time. Law school seemed to be the clearest path to working for yourself, because a lot of lawyers end up owning their own law firm, having equity in those law firms, and being their own bosses.”

Following his undergrad, Crowe went to Suffolk University Law School in 1992. He realized a year in that “practicing law was not for me,” and after his first internship, he decided to pursue business and entrepreneurship. It was during his second year of law school that he would get his first taste of this world, when he answered a job posting for a company called CRA Managed Care (now Concentra) looking for a law clerk.  

clearsurance michael crowe
Clearsurance Co-Founder and CEO Michael Crowe.

When he was hired, CRA was in its growth stage and growing quickly. They were a healthcare company that applied managed care principles to automotive and workers’ compensation insurance.

After spending a few years with the company and its IPO, the CEO of the company was let go by the Board of Directors, and Crowe then decided to go out on his own and, for the first time, try his hand at entrepreneurship. He went into business with two lawyers—Ken Paradis and Brett Albren—to start a new company in 2002: Crowe, Paradis, & Albren (later shortened to Crowe Paradis). The company, which specialized in Medicare compliance and disability services, grew “from nothing to collectively $50 million,” in less than ten years.

Crowe Paradis was ultimately sold in 2010 in two separate transactions; Verisk Analytics bought the Medicare compliance side, and insurance intermediary Brown & Brown bought the disability advocacy services business. Crowe joined Brown & Brown as SVP of Services & Acquisitions, stayed for five years, and left in 2015 to think about his next move.

“I took a good nine months off, and started to think a lot about crowdsourcing. I was thinking a lot about TripAdvisor and Glassdoor, and how crowdsourcing and user-generated content may create a better consumer experience for insurance consumers.”

Crowe thought back to his time running Crowe Paradis, when he was traveling nearly two weeks a month. In his travels, he found himself to be an early fan of TripAdvisor. “I loved the way they curated content. I felt it was more objective, so I would put a lot of stock into their hotel recommendations when I was traveling.”

After looking deeper into TripAdvisor’s business model and other review sites like Glassdoor, he went forward with the founding of Clearsurance, a review, ratings, and education community platform dedicated to auto, homeowners, and renters insurance experiences. “We wanted to distill the collective wisdom of the crowd in order to share insights on people’s experiences with their insurance companies—in a way that’s both constructive and useful”.

Clearsurance only publishes reviews once they have been vetted by their compliance team. Crowe said that the company will not publish reviews that do not meet their Community Guidelines or Terms of Use requirements. In other words, every piece of user-generated content must be from a real-life experience, and provide enough substance for a consumer to take something away from it.

Following the company’s founding in October 2015, the team built the platform and raised a $1.75M seed round in August 2016.

When they launched that December, Crowe said that the company had two key validation points. The first was to generate 10,000 user reviews in the first six months; the second was to get insurance companies to claim their profile pages. Clearsurance gives companies the ability to claim their profile for free, which includes the ability to upload a logo and other images, add basic information about their company, be notified of reviews, and respond to reviews.

For the first validation point, they reached 10,000 reviews in the first 90 days. As for the latter, insurance companies—especially smaller regional ones—began claiming their profiles very early on. “When we built the feature, we didn't think much of it because we thought it would take three to five years, and it would really just take us showing up on the first page of a Google search for any insurance company to want to engage,” Crowe said.

In February of this year, Clearsurance expanded its offerings with a new, paid subscription tier that gives companies a number of premium features in addition to those outlined above. This includes data trend analysis reports, competitive benchmarking, the ability to republish their rating as part of an advertising campaign, and the option to add a live referral link to their profile.

Clearsurance’s 17-person team is based in North Andover, Massachusetts, in the same building as the old Converse headquarters. The reason why they chose North Andover, Crowe said, is the engineering team. “Most of our engineering team is from southern New Hampshire, so we're finding it really easy to recruit very talented full-stack engineers who were commuting to places like Cambridge every day and didn't want to live in the car for three or four hours anymore.” 

Clearsurance Offices
Clearsurance's Office Decorated with an Old Mural From Converse

Crowe feels good about the current state of the business. The company raised a $4M Series A in October 2017, and over the next year, he plans to focus on both the product and the customer experience. Moreover, he plans to add four new hires to the team by the end of 2018.

When Clearsurance was first introduced to the public a little more than a year ago, I mentioned that a core validation point was to get 10,000 reviews on the platform in six months. Not only did they achieve that goal in half the time, but today—just over a year later—the community has nearly 85,000 reviews for more than 350 different insurance companies, and 45 insurance companies are subscribed to the Clearsurance community.

At this point, it’s safe to say that Clearsurance’s mission has been validated, and one hopes that being the first mover in this space will be the headstart the company needs to scale to the level of success of TripAdvisor, the Needham travel ratings giant.

Alexander Culafi is a Staff Writer for VentureFizz. You can follow him on Twitter @culafia

Images provided by Clearsurance.

Get to Know... Joe Cuccinelli, Co-Founder and COO at Photo Butler

August 31, 2017

Get to Know... Joe Cuccinelli, Co-Founder and COO at Photo Butler

Born and raised in New Jersey, Photo Butler Co-Founder and COO Joe Cuccinelli was heavily influenced by his home life. His father owned a textile mill, and his mother worked in accounting.

“I ended up developing my skill set from both of them. My father had a very ‘work hard, play hard’ kind of mentality, and I learned the ins and outs of how to run a business from him,” Cuccinelli said. “My mother, who was on the accounting side, was actually the influencing force in having me focus on accounting in college.”

Cuccinelli studied at Seton Hall University, graduating with a bachelor’s degree in accounting. His heart, however, was elsewhere.

“I studied accounting in school, and I was good at it because I have a very analytical mind, but I didn’t have much of a passion for debits and credits. I pivoted into more of a consulting role in order to transition into something a bit more solution oriented. That’s when I worked for Deloitte and switched from audit to their consulting group.”

After six years at Deloitte, Cuccinelli ended up working in NYC for Viant, one of the premier web consulting firms from the dot-com era. One of the company’s main clients was a startup in Boston called Upromise, which hired him directly and moved him to Boston in 2000.

“I went to Upromise because of the people and culture there. It was just a great opportunity to get involved in the startup scene, and I stayed at the company for five years.”

Joe Cuccinelli Photo ButlerCuccinelli says that Upromise gave him the opportunity to learn from a variety of different mentors, like Sheila Marcelo, now the CEO of, Jeff Bussgang, now General Partner at Flybridge Capital Partners and George Bell, who was CEO of Upromise at the time. Upromise was also where Cuccinelli met his wife, who was working in the company’s marketing department at the time.

“Of all the amazing things that happened at Upromise, that’s definitely my number one.”

While at Upromise, Cuccinelli led the launch of the nation’s largest grocery platform, with the technology still being used by SavingStar (which spun out of Upromise) to this day. He was also there for the launch of a co-branded credit card, as well as an online shopping mall (this business model was the foundation for another spin out company called Cartera Commerce). In addition to all this, Cuccinelli’s team was doing card-linked offers a decade before it was popular to do so.

In 2005, Cuccinelli was introduced to Jeff Glass and his team at m-Qube, and there was an “instant connection,” assisted by the fact that Cuccinelli was looking to get into the mobile space at the time. Cuccinelli was responsible for m-Qube’s Gateway product, and he was there when Verisign acquired the company. That was when he met both of his Co-Founders at Photo Butler, David Benaim (Director of Client Solutions, m-Qube) and Andy Goldfarb (board member, m-Qube).

Following the Verisign acquisition, Cuccinelli joined Eswar Priyadarshan and Andy Miller (one of the founders of m-Qube) at Quattro Wireless, where he led product. Quattro was a pioneering company in the mobile web, building sites for organizations like the NFL and NHL, and helped bring mobile advertising into the present.

“At the time, people wanted to advertise on mobile websites – WAP sites – but there wasn’t a ton of good content out there. What Quattro did was put a lot of focus on hooking up with these premium brands and publishers to turn their website content into rich, engaging mobile content.”

Because Quattro was building mobile websites for premium content publishers, this piqued the interest of advertisers, as many big brands launched exclusively in Quattro’s network. Turnkey solutions made it easy for agencies to divert their online marketing dollars to mobile.

Quattro found itself in a really good position as the iPhone had just launched, with a stable customer base of brands and agencies. Apple was looking for opportunities to expand its mobile capabilities and acquired Quattro in early 2010.

Quattro Wireless CEO (Andy Miller) breaking the news to the team that Apple was buying the company
Quattro Wireless CEO (Andy Miller) breaking the news to the team that Apple was buying the Company

“When we were acquired by Apple, we still didn’t know what we were going to launch with them. There were two-and-a-half weeks where we were working on pitches for rich media ads. Andy Miller did our first presentation for Steve Jobs, and after a couple of iterations, we knocked it out of the park.”

Working with Apple’s creative team, the group at Quattro was responsible for designing and launching the company’s iAd product.

Cuccinelli worked with Apple until November 2010, when he took an opportunity to become VP of Product at Bluefin Labs. An MIT Media Lab spinout, the company was a social TV analytics platform that measured how consumers respond to advertisements. The company was later acquired by Twitter.

Cuccinelli went on to work with Sheila Marcelo again at as their VP of Product, while they were still privately held. During his time there, he led a number of strategic initiatives. He re-launched Care’s mobile strategy, grew the product management team, and helped set their strategy around organic growth on social.

Cuccinelli was interested in getting deeper into Facebook advertising, and an opportunity to do so came along with Nanigans; they were one of the first companies to have access to the Facebook ad platform. While heading up product, he helped turn their business from a managed service to a SaaS business.

After nearly two years at Nanigans and over twenty years of professional experience, he decided it was time to start his own business.

“My wife and I were talking about it for years. I really started to get infatuated with the live, interactive elements of Periscope and Meerkat. I really wanted to find a way to bring commerce and live, interactive, video streaming together.”

This resulted in a year spent developing iWannaSeeIt, Cuccinelli’s proposed solution to this market. He bootstrapped the company, and launched a number of pilot customers.  

“It’s hard to start your own company. It’s an emotionally, taxing process, and at the end of the day, even though we had some success, I was talking to Andy Goldfarb, and his vision for Photo Butler was so compelling that it was time to press pause on my project.”

Photo Butler’s team is comprised of fifteen people, including the three co-founders, Goldfarb (Chief Butler), Cuccinelli (COO), and Benaim (CTO). Goldfarb is also a co-founder and managing director of Globespan Capital Partners.

“Andy provides a lot of the direction, while David and I are really focused on defining what it is we’re building, and executing it along with our team.”

Photo Butler, which launched last week on iOS, is a free mobile application that allows you to share photos in real-time, collaboratively, at public and private events.  

Photo Butler Mobile Screenshot

“The average person takes 2-3 seconds to take a photo and 30-45 seconds to share a photo. We eliminate that second part of the equation because we make it happen automatically. This allows people to be present and free of distraction.”

In the app, event hosts set up a photo-sharing stream and invite whomever they want to join it via invite code or SMS. When the event starts, all invited parties are instantly notified that the stream has begun. From there, photos are shared to the stream instantly, as soon as they’re taken.

It’s Photo Butler’s algorithms that really kick the app into high gear. For example, at a wedding, a guest might take between 500 - 1,500 photos. Photo Butler will automatically detect the top 200 - 300 photos. This ultimately leads to a greater level of engagement, in terms of the average number of photos that consumers will view and save to their phones.

In addition to saving photos, users can share them on social platforms like Facebook and Instagram. The event owner is given complete control over photo streams; only they can decide who gets to view or contribute to the album.

Cuccinelli says that Photo Butler is focused on growth in 2017 and monetization in 2018, considering different B2B and B2B2C options. However, at the moment, the company is ultimately taking a measured approach to growth.

“At the end of the day, if you have a good product, those opportunities will present themselves.”

Cuccinelli wants Photo Butler to transform the event experience.

"Imagine never having to ask someone to text you a photo. And think about all those group shots where you have to ask the person taking the photo to take just one more with my camera. With Photo Butler, everyone is connected, collaborating, sharing and contributing. Everyone stays in the moment free of distraction. We’re delivering an app that's changing the way the world shares memories."

Alexander Culafi is a contributor at VentureFizz. You can follow him on Twitter @culafia.

Get to Know… Kevin O’Brien, Co-Founder and CEO of GreatHorn

July 17, 2017

Get to Know… Kevin O’Brien, Co-Founder and CEO of GreatHorn

Growing up in Leominster, Kevin O’Brien started out writing code on a Commodore 64. In the late-80s, O’Brien subscribed to computer programming magazines, where he learned to program thanks to the interactive stories. “You had to finish the program to see how the story ended and it was written in BASIC,” O’Brien remembers. “It was obviously designed to teach children how to code.”

In his college years, O’Brien kept his interests laid in tech, but did not go for the usual computer science degree. Instead, he studied a variety of subjects, including philosophy, film and world languages. O’Brien also began another outside interest; practicing martial arts, specifically the Japanese martial art Aikido.

Kevin O'Brien practicing Aikido.
O'Brien practicing martial arts. O'Brien is also an Aikido instructor.

Throughout his time at UMass Amherst, O’Brien worked for an early-stage security startup, @stake. “I got the ‘bug’ so to speak,” O’Brien remembers. “It solidified my interest in startups and deepened my interest with cybersecurity.”

Working in early-stage startups started to become a recurring theme for O’Brien’s career. After graduating UMass Amherst, he was hired by QAS and then, Contact Networks. Both companies were later acquired by Experian and Thomson Reuters respectively.

In 2012, O’Brien moved to working with CloudLock, where he held a variety roles, including as a Senior Solutions Architect as well as Director of Product Marketing. Another cybersecurity company, CloudLock was recognized as an early innovator of cloud-based security, helping define the concept of Cloud Access Security Broker (CASB) solutions, as well the concept of aligning security software with business objectives rather than impeding them.

At this Waltham-based startup, O’Brien not only helped increased revenue with his marketing know-how, but he also served an industry expert contributing to several media outlets, including Wired, CISO Magazine, and NPR Marketplace. He also started working the conference circuit as a speaker. CloudLock would later become acquired by Cisco.

After CloudLock, O’Brien joined the founding team at Conjur in 2014 as a Vice President where he built out and led the core marketing and sales team. The company just announced its acquisition this past May.

As you might have noticed, there’s a common theme for the companies that O’Brien has joined. Each company was ultimately acquired at some point. So, how does he keep picking winners? “It’s part luck, part science, and part heart. There’s no single formula; what makes a startup work out is the people who are doing the day to day work. I’ve been lucky to be part of incredibly smart, passionate, dedicated teams,” says O’Brien. “I try to look for organizations that are honest, sincere about what they are doing, and where the timing is right.”

His interest to start his own company was sparked by observations and experiences within the security industry: O’Brien noticed how socially engineered cyberattacks, phishing, and account compromise attacks are increasing, especially as technical infrastructure continues to change and expand.

“We are in a moment of transformation. Cloud applications have created an always-on culture, and organizations and their employees are constantly in contact with each other, whether that’s via cloud-based email platforms like G Suite from Google and Microsoft Office 365, or via new so-called “chat-ops” systems like Slack and Teams,” says O’Brien. “Increasingly, the lines are blurring between what constitutes “work” and “life”, between corporate IT and employees’ personal phones, computers, and even online profile.”

It is this new world which led O’Brien to take the leap of faith to start GreatHorn with his co-founder, Ray Wallace, a friend since his high school days. The duo bootstrapped the business for the first year, renting their first offices on personal credit cards and drawing down savings while launching the first version of the platform, which provides the first cloud-native, fully automated security solution for stopping targeted phishing, email compromise, and social engineering attacks.

As they began to find traction with early customers, and began considering outside capital, an introduction to Alex Iskold, Managing Director of Techstars’ NYC accelerator, was made. As serial startup veterans, they were initially skeptical of pursuing an accelerator, but the opportunity to deepen their networks beyond the Boston area was compelling. They were accepted, joined the Fall 2015 cohort, and packed their bags to move into a small apartment on the Upper East Side along with Chris Fraser, GreatHorn’s VP of Strategic Accounts and final member of the founding team and former colleague of O’Brien’s at both CloudLock and Conjur. The trio used their time at Techstars to drive continued growth and adoption by new customers.

O'Brien out on the seas!
O'Brien out on the seas!

Social engineering attacks are historically the most effective form of cyberattack, because they don’t rely exclusively on technical trickery to work their past perimeter defenses. O’Brien noted that during the early part of his career, security teams hired to test clients’ defenses could often get access to server rooms by impersonating as a UPS employee, relying on someone holding a door when the “attacker” was laden down with packages.

Today’s attacks leverage the same concepts of using social cues and urgency to play on a person’s desire to be ‘good.’ For example, a hacker can impersonate as the CEO of a company and request time sensitive information from a lower-level employee. What does the employee typically do? They likely reply back to the message, which opens the doors for the hackers.

“Unfortunately, we’ve see that kind of attack surge,” the cybersecurity veteran says. “By combining that social pressure and psychological pressure with various forms of spoofing and manipulation on what an email looks like, a data breach happens.”

He adds, “93% of data breaches occur with some form of phishing attacks.” Several outlets, including Intel Newsroom and Digital Trends also report similar findings.

Today, GreatHorn’s solution helps companies secure email, chat, and collaboration platforms and communicate with confidence. Over the past year, the company’s revenues have grown 565% and just last month, GreatHorn raised over $6 million in capital in its Series A funding led by .406 Ventures and Techstars Ventures, putting the total capital raised by the company at just over $9 million.

O’Brien is passionate about expanding the Boston cybersecurity market. “We are deeply interested in how people think, and intrigued by the ‘why,’ behind effective cyberattack schemes” O’Brien says. “Cybersecurity ultimately comes down to a the intersection between high-technology and basic human psychology.”

Colin Barry is a contributor to VentureFizz. Follow him on Twitter @ColinKrash.

Images courtesy of Kevin O'Brien and GreatHorn.

From PhD to CEO, Elizabeth Lawler Takes on Cybersecurity at Conjur

May 8, 2017

From PhD to CEO, Elizabeth Lawler Takes on Cybersecurity at Conjur

Elizabeth Lawler uses her background in the sciences to give her a leg up when it comes to fighting cyber warfare.

When it comes to stereotypes, Elizabeth Lawler breaks through them. Unlike most CEOs in the Boston area, Lawler did not graduate from MIT Sloan or Harvard Business School. She did not start her career at Deloitte or McKinsey & Company. Elizabeth Lawler instead gained her PhD in Epidemiology and began her first career as Director of Pharmacoepidemiology Research at VA Boston Healthcare Systems.

In 2011, Lawler went from fighting disease to fighting on the cybersecurity front when she became the Co-Founder and CEO of Conjur, a now 4-year-old Waltham-based data security company.

From PhD to CEO

Just because you are the director of research at a government funded facility does not mean starting a business is any different. Elizabeth Lawler co-founded Conjur in her living room, on a card table, just like everyone else. It wasn’t her first experience in entrepreneurship, but it was her first time taking on the role of CEO. Though Lawler rarely referred to herself as CEO back then, she instead wrote “resourceress” on her business card. Understandably at the time, Conjur was a very early stage startup and her job, as she saw it, was to find resources.

Step number one was to find resources, step number two, she had tattooed on her body. It was a piece of advice given to her by her mentor Andy Palmer; “Don’t Run Out Of Money.”

It was Lawler’s adherence to these two simple rules that allowed her to move from PhD to CEO.  It was her focus on culture, customers, and product that paved the way for her success as a business leader.

Party Hats and Razor Blades

Starting a new company is a challenge. Early stage startups, as Lawler puts it, often fall into the mindset of party hats or razor blades.

“You feel like you’re either celebrating or you’re going to die. Surviving in that state of mind means balancing the difference between how you feel in the moment, your confidence in your strategic direction and ability to execute.  That centeredness helps you project calm, urgency without panic,” says Lawler.

Learning to ride the startup roller coaster was just one of the challenges Lawler faced when beginning her enterprise. The biggest lesson she learned was a quote by Peter Drucker, "Culture eats strategy for breakfast.”

Lawler often uses the word safety when speaking about Conjur. A word not often used by software professionals, it’s a throwback to her epidemiology days. And it’s not just a word she brings up when talking about the latest data breach or hacker news; it’s the word she uses when talking about company culture.

“I think culture is probably the most important thing a CEO can tend to in the day-to-day operations,” says Lawler. “One of Conjur’s core values is safety. We want to create a safe environment for people to be themselves. I wasn’t actively driving culture in the early days, and people weren’t listening and being tolerant. That was a huge lesson for me. Now I spend a lot more time ensuring that Conjur is a safe and positive workplace.”

Not Your Everyday CEO

Lawler’s background gives her an uncommon perspective on how to run a business. She defines her personal leadership style as “the gardener.” Preferring to plant a seed and watch it grow. A direct contrast to the hands-on leadership style practiced by many of her peers. She goes on to explain that at the beginning of Conjur, she would get called into every decision. As the company grew however, she needed to add in points of elevation – delegation. Giving her employees room to grow, Lawler doesn’t micromanage. According to her, too much love can kill even the most hearty of plants.  

Now that Conjur has surpassed many of the major battles a startup faces in their first years, Elizabeth Lawler has begun to reflect on the many similarities between her work as a PhD and a CEO.  “It was the turn of the 20th century when we started making medical standards such as clean bandages and washing hands,” says Lawler. “I think it’s time to create standards for cybersecurity too.”

It is this kind of mindset, one so far away from the ordinary business dialogue, that makes Elizabeth Lawler a unique and successful business leader.

Necco Ceresani is a contributor to VentureFizz.  Follow him on Twitter: @Necco_C.

Images courtesy of Elizabeth Lawler.

Recognizing Opportunities - Andy Cook, Co-Founder and CEO of Tettra

April 24, 2017

Recognizing Opportunities - Andy Cook, Co-Founder and CEO of Tettra

The best piece of advice Andy Cook, Co-Founder and CEO of Tettra, can give to young entrepreneurs is, “Don’t start a startup.”

Launching his own company never seemed to be a question in the mind of Cook. Growing up in Hanover, Massachusetts, Cook has had an entrepreneurial spirit since the age of 10 when he started his first paper route. Being raised by his mother, a teacher, and his father, the owner of a landscaping company, Cook grew up watching his father run a successful business for 35 years. As a child, Cook dabbled in his own endeavors, everything from hawking weekend newspapers outside his local Dunkin’ Donuts to collecting cans with his brother to recycle. Recognizing opportunity has always been one of his strengths.

Learning To Be a Founder

Anyone in the startup world will tell you that starting your own company is one of the most difficult, and stressful, things a person can do with their career. It’s even harder to start a business while you are still in college.

In 2010, while at UMass Amherst, Cook and his older brother Alex built an online rental marketplace called Rentabilities. The idea originated from an online booking system Alex was building for a local rental store owner. The site ended up generating tens of thousands of dollars worth of bookings in its first year, which opened the opportunistic eyes for the two brothers.

After looking at the market some more, they realized that renting anything from a bounce house to a lawn mower was a total pain. It was an underserved market which hadn’t been disrupted by an online model yet.

“We thought we could put it online, like a GrubHub for renting lots of different items,” said Cook.

It was a clever idea, but they needed more resources to execute on it. Luckily, they heard an ad for the first ever MassChallenge competition on the radio and decided to apply. It paid off, as they ended up winning $50,000 to help fund the business.

While at MassChallenge, Cook attended a talk which was given by Dharmesh Shah of HubSpot. He took notes from Shah’s discussion which he later published as a blog post outlining all the different startup lessons he shared. This ended up starting a relationship between the two of them and as they were raising additional capital, Shah participated in their seed round of funding.

Cook and his brother worked on the business for three years, but hit the wall with the Series A funding crunch. It was difficult to attract investors for the industry they were servicing and they eventually sold the business to HubSpot as an acqui-hire.

One of Cook’s biggest takeaways from running Rentabilities, and advice he would give to other founders, is to focus on solving problems that you can relate to. Ultimately, he wasn’t the site’s demographic, as he didn’t have the need to rent anything.

“It was hard to get into the head of the user and grind it out when I couldn't really even use our own product,” said Cook. “When the going gets hard, and trust me it will, solving your own problem really helps because if everything else implodes, at least you’re making your own life slightly better.”

Don’t Start A Startup… Unless…

When a second time entrepreneur tells me his best advice to young founders is, “Don’t start a startup,” a hypocritical eyebrow raises…until he explains the idea behind solving your own problems.

“Only start a company if the idea you want to solve is so compelling to you personally that you have to make it a reality,” says Cook. Not only is this great advice from Cook, but it is also echoed by Dustin Moskovitch (Facebook co-founder) in a recent presentation at Stanford’s Startup School.

Tettra Team Photo
Tettra Team Photo

Cook is practicing what he’s preaching with his latest company, Tettra, which is creating a wiki for Slack teams. Cook and Nelson Joyce, his co-founder, discovered a pain point while trying to keep their small team at HubSpot on the same page. They were interested in using an online wiki. But to their surprise, a solution didn’t exist… at least something that was simple and designed for small teams.

Again, recognizing an opportunity, both Cook and Joyce left HubSpot to build out their own wiki solution. They had to iterate quickly on the product based on some early feedback from teams testing the product. They realized a stand-alone application wasn’t going to have the right level of user adoption. Instead, it would be better if their wiki was integrated with another commonly used product that already had widespread adoption.

The timing worked out, as it was right around the same time that Slack launched their platform for external developers. They rebuilt 100% of their entire product on Slack and started getting an impressive number of signups, which validated the market and opportunity. They went on to raise just shy of $1M in funding from Dharmesh Shah, David Cancel, Mike Volpe, BOSS Syndicate, and a who’s who list of investors.

“First time founders have it tough, especially if you are looking to raise capital, because you’re learning so much in terms of building a company from scratch, all while trying to figure out how to make something people want. They must build out their professional network and also create a successful company (and ultimately organization) in extremely difficult circumstances,” says Cook. “If I could do it over again I would have worked for a startup that was scaling right out of school to learn and build relationships, then I would have gone out to start my first company.”

Two other pieces of advice from Cook is to find great mentors and stay scrappy. Great rules to live by for any first time founder.

When discussing his entrepreneurial journey so far, Cook remains very humble and realizes he still has so much to learn.

“I've found in life that the more I learn,” says Cook. “The more I realize what I don't know and have so much more to learn.”

Necco Ceresani is a contributor to VentureFizz.  Follow him on Twitter: @Necco_C.

Hat tip to the Tech in Boston podcast interview with Andy Cook which was used as part of our research.  Listen to the full podcast here.

Taking Risks with Jonah Lopin, Crayon's Co-Founder and CEO

April 4, 2017

Taking Risks with Jonah Lopin, Crayon's Co-Founder and CEO

​Whether it’s dropping a successful career to travel across the world or take a chance on a risky new startup, Jonah Lopin is one CEO who is not averse to risk.

Jonah Lopin, co-founder and CEO of Crayon

Son of an electrical engineer and teacher, self-admitted nerd and now co-founder & CEO of Boston-based startup Crayon, Lopin is not what you might expect after reading his LinkedIn profile. Using words like flirt and play when talking about his first experiences with computers at the age of six, it’s not so hard to see why Lopin found his place amongst the software elite from a young age. After leaving his job at Deloitte to volunteer with UNICEF in Beijing, and then finally receiving his MBA from MIT,  Lopin found himself not taking a job in international investments, but risking everything as the 6th employee at a startup with unbounded potential.  

The HubSpot School of Hard Knocks

No matter what education or background you come from, taking a “senior” position at an early stage startup is extremely risky. But for Lopin, padding a resume with middle management jobs was never in the cards. His personal business philosophy comes in two forms, “I want to build something big that changes the world,” and “I was to use my time on planet earth not to avoid risk but to create new things.” It’s this philosophy that lead a young Lopin to taking a job, at one-third the salary other companies were offering, and building an enterprise that would change the software world forever.

“I think any good executive can learn as she goes and make up for inexperience with tenacity, good coaching, luck, etc. Relevant experience just makes things easier,” says Jonah Lopin in an interview earlier this week. His experience just so happens to be ‘the HubSpot School of Hard Knocks’, as I like to refer to it. Six years of hard-won lessons building a crazy vision from the ground up has given Lopin three business lessons he takes everywhere he goes.

1. Every new hire should be better than the average of the people already at your company.  If you can’t keep that up, your average declines over time, by definition.

2. Many mistakes will be forgiven as long as revenue grows. We got lots of things wrong in the early HubSpot days, but one thing we got right, really right, was we cracked the code on a repeatable sales & marketing process that enabled us to grow quickly.

3. Whenever possible, use data to make decisions.

It was these three lessons that set up the foundation for Crayon, Lopins latest software adventure. Crayon solves the problem of prioritizing, organizing and analyzing new data coming from your competitors.

The Makings of a Great CEO

If experience makes life easier, it’s hiring that makes Lopin successful. “The number one thing is that I’m a good recruiter,” Lopin says. “I’ve hired over a hundred really good people in my career and the team I’ve recruited for Crayon is top notch. It’s not easy recruiting top talent to an early stage company. It’s all about being able to explain your vision. The other part of it is having a good instinct and a process for finding the stars. If the 5th person you hire isn’t the right person, 20 percent of your company sucks for at least a year.”

At the end of the day, starting and running a successful company isn’t about being a great recruiter or having the most experience. The CEO of a company must possess an innate drive to create their own vision. Jonah Lopin is the type of person who succeeds because he, even after being a founding member at HubSpot and creating the immense visions of Dharmesh Shah and Brian Halligan, decided to put his career on the line again to build his own vision. This, at the end of the day, is what separates so many from so few.

Necco Ceresani is a contributor to VentureFizz.  Follow him on Twitter: @Necco_C.

Passion is a Requirement with Jason Furtado, Founder & CEO of Shoobx

February 21, 2017

Passion is a Requirement with Jason Furtado, Founder & CEO of Shoobx

In the face of complexity, first time CEO and founder, Jason Furtado, doesn’t shy away from the hard problems.  

Three years ago, he started Shoobx along with Stephan Richter, to provide a comprehensive platform for startups to manage corporate legal activities around things like company formation, fundraising, and other important foundational aspects of a company. It was an industry that was ripe for disruption, but not an easy one to change.

Walking Off the cliff

For Furtado, the fear of failure never goes away. Once Furtado recognized that was the only thing holding him back, there was no way he was going to let fear get in the way of his success. It was at this point that Furtado decided that instead of jumping to another large company or a small startup, he was going to venture out on his own and solve a real-world problem.

Jason Furtado, ShoobxTo Furtado, solving a problem doesn’t necessarily start with industry experience, “I walked into Shoobx as a first-time CEO knowing nothing about corporate law, venture capital or equity for that matter, but planning to change how the innovation ecosystem works.” Even though Furtado lacked relevant experience in the problem space, he did know how a successful development organization works and how products are built for growth. Before starting Shoobx, Furtado worked as a product manager and was part of the special operations team at Endeca (acquired by Oracle in 2011).

Changing how an ecosystem or an industry works is risky. Basing your future profits on your platform’s ability to change behaviors inside that ecosystem might be considered irresponsible. But big problems need big solutions, and Furtado doesn’t believe all problems can be solved with narrowly focused MVPs.

Furtado realized that too many solution providers were attempting to dig a big hole with a little shovel. Changing an ecosystem takes a lot more than simply optimizing existing activities. Contrary to the popular belief of the lean startup, Furtado says “Once you identify the right problem to solve, the MVP required to get traction might take a lot of investment.”

Facilitating Success

Not unlike most first time CEOs, Furtado struggles with his cravings to roll-up his sleeves and jump into the trenches. “I still commit code, but my team will call me out for taking on projects I shouldn’t take. They keep me accountable just as much as I keep them accountable. You set the example, but that doesn’t mean you do all the work.” 

Jason Furtado, ShoobxFurtado believes the most important job of a startup CEO is to facilitate his team’s success. When building a team, Furtado focuses on making their customers successful and letting that guide them as they collaborate. “I think being the CEO of a startup is a crazy thing to do. The first step to keeping above water is recognizing that it’s not all about you. You need to rely on your team.”

“It’s more important to have a balanced core team with diverse experiences than one perfect person to give yourself the best chance of success,” said Furtado.

Being a young CEO often means making mistakes, but it’s Furtado’s passion that drives his young startup towards success.  

Necco Ceresani is a contributor to VentureFizz.  Follow him on Twitter: @Necco_C.

Achieving Unique Goals with Zorian Rotenberg, Founder & CEO of Atiim

January 5, 2017

Achieving Unique Goals with Zorian Rotenberg, Founder & CEO of Atiim

Success for a startup CEO is making those who believed in you look brilliant (customers, employees, and investors). This reference to a quote by Dharmesh Shah is how Zorian Rotenberg describes his job as first time startup CEO and Founder of Atiim. Coming from humble beginnings, behind the iron-curtain in Ukraine, to Harvard Business School, and now running a growing software startup in Boston, Zorian is far from your typical business leader. 

A Good-Relationship Person

When I asked Zorian if anyone could be the CEO of a startup, he responded with a joke - “Only if you love pain”.  As Zorian describes the job, it’s a Venn diagram that shows four circles: taking a huge personal risk, facing intense challenges, working 100-hour weeks and taking little or no pay. It takes a specific type of person, one who has a desire to go far out of their comfort zone, to start from scratch, to take on an infinite number of challenging obstacles, do it all on limited resources, and yet enjoy that experience. To Zorian, starting and leading a startup is less about liking the pain and more about achieving challenging goals. It’s about doing something fulfilling, all while becoming a little bit better and wiser. 

The difference between Zorian and other company leaders is instead of separating work and life, he embraces his life experiences to help him become a better leader. Who in history inspires him? His grandmother. She had the courage to leave the Soviet Union all alone in order to make it possible for Zorian (with his parents) to immigrate to the U.S. during the Cold War. What kind of leader does he try to be? One focused on building good relationships, because good relationships are ultimately the point of life itself. And how does he stay sane in such an intense job? Being thankful every day for his family, working out before sunrise, and also keeping a perspective in life. When you immigrate to the U.S. with just $200, can’t speak English, you have to work really hard to get anywhere. You struggle when you’re growing up so everything gets easier compared to your earlier experiences. It is that type of perspective that makes Zorian‘s journey unique. 

The Secret Sauce  

Zorian has a unique set of experiences to draw from, having been a VP running both Sales and Marketing on the management teams of some of the highest-growing and most successful software startups.  He was a VP of OEM Sales & Business Development at Acronis which grew from $20M to $100M in just 3 years.  At Veeam, he was VP of Demand Generation, which is one of those super rare companies that went in 10 years from zero to well on its way to $1 Billion in annual sales.  Prior to starting Atiim, he was the VP of Sales & Marketing at InsightSquared.

Zorian only had one answer to the proverbial question as to what drives results: Teamwork.  Being a Bill Belichick and a Patriots fan probably contributes to his belief that building a company is a team sport. “Alignment” across the company is one of the few true competitive advantages and the secret sauce that drives results of best-performing companies.  In fact, Zorian current startup Atiim (pronounced as “A-Team”) supports his philosophy. Their product called Atiim Pulse OKR is all about creating internal alignment and driving higher performance by letting companies set and manage their objectives (rooted in the OKR (Objectives & Key Results) approach which Google made popular) and align everyone’s efforts at the company to the CEO’s top goals.

While alignment contributes to Zorian’s secret sauce, he also knows that the CEO’s job at an early stage startup differs from that of billion dollar companies. He breaks down his “startup CEO” role today into 6 categories: 

  • Strategy & Execution – The CEO must set the vision, must know how to get his company there, and must execute and manage operational execution towards that vision (which at an early stage is a ton of arduous work without resources). 
  • Recruit A-Players – Build out a great team (that’s 80% of the battle).
  • Sales – The CEO must be the first sales rep of the company and needs to build a predictable and repeatable process that scales sales with newly hired sales reps.
  • Marketing – The CEO must do the marketing to get those leads into the sales funnel… he must evangelize the company and then do something innovative to be able to build a cost-effective customer acquisition funnel.
  • Cash – It’s all about growing sales while keeping a laser focus on managing money effectively.
  • Resourcefulness – this is the least talked about role of a startup CEO but this one is probably the most critical success factor of a startup CEO and is far more critical than for someone who is a CEO of a billion dollar company.

Advice for the Hard Times

Challenges and hard times always come with the territory when you start a company. Even the best businesses in the world go through that. How a company leader deals with these situations is a determining factor for the long-term success of any company. When asking Zorian about the hard times that startups experience during their early stages, he quotes Winston Churchill and Bill Belichick, “If you’re going through hell, keep going”and “Do your job!”  It’s all about hard work, staying tough and positive, and having a laser focus on your goals ahead – this is the recipe for handling startup challenges.

If there is one thing to take away from Zorian and his current legacy as an analytical minded CEO, it’s that anyone can go to school, learn to read numbers and surround themselves with an amazing team of people. It is your life experiences and how you let them inspire you that sets you apart from the rest. 

Necco Ceresani is a contributor to VentureFizz.  Follow him on Twitter: @Necco_C.

Curata’s Pawan Deshpande on How to Make Startup Magic Happen

July 7, 2016

Curata’s Pawan Deshpande on How to Make Startup Magic Happen

This post appears as part of our Driven profile series, spotlighting some of the hottest movers and shakers from all corners of the Boston tech and startup space. Know someone we ought to chat with? Let us know

It’s safe to say that any B2B marketer worth their salt today understands the value and invests in content marketing. In fact, a whopping 88 percent of North American B2B marketers use content marketing and 51 percent plan to increase budget for it in the next year. What’s more, it’s estimated that over half of all companies will have an executive-level role dedicated to content by next year.

Think back just a few years, though - as recently as 2010 - and the term “content marketing” was barely recognized. Securing budget for it wasn’t easy. Many companies didn’t understand the value of investing in in-house content marketers or software to help support content-related functions.

It was at this time that Pawan Deshpande, founder and CEO of Curata, launched his company. Today, the software helps marketers analyze content’s impact on business, build a stream of steady content, and create efficient content production processes. In the last 18 months, it’s more than doubled in size, from just 12 employees to now over 40.

I recently sat down with Deshpande in his office on Tremont Street to learn more about Curata, why he opted to pursue content over other forms of marketing, and how his company has kept up with the industry’s evolution. Read more in the interview below.

Kaite Rosa: You and your company were early players in the content marketing space. What made you pursue this marketing route versus other aspects of digital marketing?

Pawan Deshpande: In 2007, I started the company with my freshman year roommate from MIT. We knew a lot about tech, but we didn’t know anything about content marketing. I don’t think content marketing was even a phrase yet, then.

Our initial idea was for a consumer app. The basic premise was that if you were interested in a specific topic - puppies, for example - we would aggregate content on that topic. The business model was that we’d put ads on the side that was relevant to the content. So, if the topic was puppies, then you’d see ads for dog food, dog toys, etc.

We found that the tech worked really well. We got a lot of good content on there. But we weren’t getting a lot of visibility or traffic. The everyday hobbyist doesn’t know how to market an online destination. So we started looking at other business models: media monitoring, competitive intelligence, we beta’d with some marketing departments. It worked, but the business value was relatively low. A lot of execs will look for five seconds at an email and then delete it.

Then, an early customer shared it externally to their broader industry. The customer didn’t want to blog and be more noise. He wanted to make an online destination just about this topic. Within a few months, they were the go to blog. This was before curation, before content marketing existed. That’s how we landed at this business model.

Then, in 2010, we validated it. The customer said he’d pay $1K for our software. That was the real “aha!” moment that there was some business value here. We said, “This is real. Let’s launch the company.”

KR: Content marketing has rapidly evolved since its early days. What types of challenges has this presented you and your business? How have you in turn evolved to keep up?

PD: I think it’s more than challenges. Instead it has been about opportunities. People now know what it [content marketing] is. Sales cycles have shortened dramatically. Companies hire people with “content” in their title - which wasn’t the case in the beginning.

The challenge to the market is that now there’s more noise out there. Everyone says they do content marketing, but we’re all different players within it. There’s also lots of mediocre and poor content out there. Both our products address that. Data and analytics surface up which of your content is performing well and the curation shows the best content out there.

KR: You’ve grown Curata pretty steadily over the past six-plus years. How have you built your team? What’s your leadership mantra?

PD: When we started company, it was just me and my roommate. Now, we’re at 40 employees.

I have played every single role in the company at some point. I enjoy doing all parts of the company, but I also enjoy bringing in people who can do those parts. I hire people who can do them better than I can. But if I need to, I can still work closely and dive in.

I like to sit out there on the floor and work with different departments for 6 months [at a time.] A few months ago, I was working with the sales team on how to pitch product. Now, I’m working with customer success.

Overall, building a company is about this: You’re only as strong as your weakest link. Look ahead of what’s coming and focus in on what that weakest link may be.

KR: What are some of the biggest lessons you’ve learned from starting and growing your own company?

PD: They often say that if you build a better mousetrap the world will beat a path to your door. That’s naive. It’s a lot more than just building a mousetrap.

You need to make sure someone is willing to buy the mousetrap and that the mousetrap solves a problem in the market. And then there’s sales, marketing, supporting customers.

Most of the challenge is in the execution, rather than just building a better mousetrap.

KR: Thanks to your father, Desh Deshpande, you’ve had entrepreneurial exposure from an early age. What was your childhood like and how did it influence your career path today?

PD: In elementary school and middle school, I spent weekends at my father’s office. I would be there, using their high speed internet to download games and using the color photo copier. I always remember him working weekends. That was common and it had an influence on me.

Here’s one key piece of advice he gave me: If you have a B product and an A team, or an awesome product and idea but a B team, the A team always wins. The A team can always evolve the B product.

Otherwise, I think a lot of my entrepreneurship has been through my own exploration and discovery. In high school, I programmed a lot of products. My first pay check was through Microsoft Business Central. I was running my own site and had banner ads.

KR: Wow, that’s impressive. How old were you?

PD: I was around 12. I started coding when I was 9. A lot of that is self-ambition. But in terms of formalizing and scaling it [Curata] and turning it into a organization, I think that’s where my father has been helpful.

KR: Has it been hard to differentiate your own personal brand from your father’s?

PD: If anything, I have been able to use it to my advantage. Early on, I didn’t have a network in the business community. It has been useful to open up doors - an advantage, if anything.

KR: Tell me about some of the unexpected challenges you’ve faced while growing your startup. What obstacles have you faced that you never anticipated?

PD: One was my role. When I started I was very naive. I was coming from an engineering background. I thought you just wrote code and the checks came in. There’s a lot more to running a company from a leadership standpoint, from public speaking, from sales. These are unexpected things that I initially shied any from. But I have come to embrace them now.

Another thing is that earlier, I didn’t trust myself as much as I should have. A lot of times, you look at someone with a lot of experience and think they know better than you.

But the founder knows their business best. The founder needs to be the best sales person, the spokesperson. That’s not to say you can’t hire people who help augment that, but you can’t expect to hire someone to make magic happen. The founder has to make it happen in the first place.

KR: What about a time you royally screwed up? Can you tell me what happened?

PD: In 2013, Google Reader was going away, so we decided to launch an alternative to it. In 60 days, we built a replacement that was highly scalable. A lot of our tech is very similar to it [Google Reader], so we know how to do it. It did get a lot of traction, it was named a top five reader by Cnet, mentioned on Slate. At its height, it had 1.8M readers.

In that way, it was a success but it had no business model behind it. We found out why Google shut down Reader.

KR: What did you learn from all that?

PD: It’s good to experiment. In hindsight, it was not a good use of resources. It was a distraction. But you don’t know where things are going to end up.

KR: Since then, what’s your philosophy on experimentation?

PD: Experimentation has to be balanced and with focus. You can’t run 10 experiments at once. With the Curata Reader, I don’t think we had an end goal in mind. We didn’t have a hypothesis in terms of how we would sustain it in the long run. In retrospect, it wasn’t a well designed experiment.

KR: What are some of your secrets for staying productive?

PD: I subscribe to the Inbox Zero methodology. I try to get to zero [emails] every day.

One of our company mottos is, “Don’t drop the ball. Pass or shoot.” That’s very important from an execution standpoint and I try to personally follow it.

I also use this template - an urgent/important matrix. Every Monday, I print it out and list what I need to do. On the flip side, I list all the departments and the items I need to cover with each team.

KR: Oh, that’s very interesting. How long have you been using it?

PD: I used to have a 1:1 management software, but I find paper works best. It’s simple. I’ve been doing it since the beginning of 2016.

KR: Last question. How do you keep it together when sh*t hits the fan?

PD: Having a good team diffuses it [the stress], so it’s not all on one person.

I’m pretty good about unplugging. When I go home, I am not constantly checking my email.. I limit that. It’s not a conscious thing. I just don’t feel the need to constantly be on top of every email and everything that happens. But I have grown to be that way. Before, I was always on.

A good analogy - it’s from someone else, not me - is that life is like juggling balls. Some are rubber balls and some are crystal balls. Drop a crystal ball, and it will never bounce back. Work is a rubber ball. Family is a crystal ball.


Kaite Rosa is Director of Content & Marketing at VentureFizz. Follow her on Twitter: @KaiteRosa

Image by Steve Hall