Episode 417 of The VentureFizz Podcast features Rob Hughes, Co-Founder of Koo Capital.
If you haven’t met Rob yet… you should. He is one of the personalities behind the Boston tech scene and he is doing his part to bring the extra energy and buzz that is brewing in addition to initiatives like the Massachusetts AI Coalition.
We need more Rob’s, as he has a big personality and it’s only fitting that he is one of the faces behind Pitch Lift, along with angel investor, Steve Walsh. Pitch Lift is a Shark Tank style elevator pitch event that literally happens in an elevator. Founders get 30 seconds to grab the attention of an investor and make an impression before the doors open. It’s a fun but high pressure environment and you can see it in action on Instagram and TikTok.
In addition to Pitch Lift, Rob is a co-founder of Koo Capital, a private credit advisory platform built by bankers for founders to help high-growth companies unlock non-dilutive capital to scale faster.
In this episode of our podcast, we cover lots of great topics:
- All the details on Pitch Lift & How it Got Started
- Rob’s background story and career.
- What led him down the path of starting Koo Capital and how they are helping entrepreneurs with alternative funding options.
- Common pitch mistakes that entrepreneurs make.
- How to create engaging and quick hitting social content.
- And more!
Transcript
Keith Cline (01:51)
Rob, thanks so much for joining us.
Rob Hughes (01:54)
It’s great to be here, Keith, wherever we are. It’s always hard to tell when you’re in these black boxes. You’re like, where are we exactly?
Keith Cline (01:57)
Hahaha
Exactly,
yes. And I have noticed that you have been traveling quite a bit because you’ve been, you’re wearing your swag PitchLift. And I was, ⁓ you know, just doing some homework before our conversation and noticed this PitchLift thing that you’ve been involved in, which is a, it’s a really, mean, it’s it’s a idea that makes a lot of sense. ⁓ And I’ll let you talk about what it is, but what I was blown away by was the content and the social media strategy behind it. It’s a great event, but.
Rob Hughes (02:09)
Yes.
Keith Cline (02:31)
the amount of content that you are creating out of it, the social media persona. So I wanted to talk to you about that strategy as it to PitchLift. And I noticed there was a pseudo celebrity like person that was participating. I don’t watch Love is Blind, my daughter does. So that’s why I knew of it. And you had like a ⁓ contestant of that show on as a entrepreneur pitching his company. So anyways, I’ll let you talk about what PitchLift is.
Rob Hughes (02:48)
Yeah.
Yeah, so PitchLift was originally born out of frustration from meeting with lots and lots of founders and spending the majority of the meeting trying to figure out what they were doing. ⁓ My ability to understand companies is pretty high compared to most because I interact with so many of them and have been doing so for so long. But it was, I was spending too much of my energy like trying to get it, like what is it that they’re actually doing? And ⁓ at the time was a big fan of the UFC.
I’m still am, but I have kids now, so I can’t stay up that late. with the fighters often talked about the physical implement of the cage and how it actually brought out different emotions and energy levels in them when they closed the doors.
And I had this novel idea of what if we put founders into elevators with VCs and had them pitch on the way up to event space. So I did one in late 2019, probably the fall of 2019 in Boston when I was running tech and VC banking for First Republic Bank on the East Coast. ⁓ we were doing okay, but it hadn’t really hit our stride. And that thing just launched us into the stratosphere and people really started talking about what we were doing and what
founders should work with us. had several million dollars of term sheets that got issued from that event and I immediately wanted to do another one and of course COVID happened and that became an impossibility. So we came out of COVID, promptly went into a bank run. ⁓ So I had a front row seat, the second greatest bank run of all time at First Republic ⁓ and learned a lot through that by the way. Went over to Citizens to help launch the private bank there and launch their tech and VC practice. So kind of repeat
the same thing and so I did a couple there with them and my good friend Steve Walsh ⁓ who helps me on who’s my co-founder of the pitch left said hey let’s take this thing on the road like let’s try to do like different cities let’s see you know we’ll do Austin we’ll do New York we’ll do LA we’ll do Miami let’s let’s try to do this and along that process we were filming all the you know the pitches we’re filming kind of getting our arms like ⁓ kind of want to do a content play here but after LA the team that I brought out to help
do this because it takes an army to get it done approached me and said hey, well you think this is like awesome this should be something we do as like content like this is a big content play. Let’s make the shark tank of the internet. Let’s make shark tank for scroll culture. Let’s bring founder pitches and these high-pressure situations and stories into the mainstream of people’s you know how people are thinking about innovation and founders and their stories and their companies they’re building. So it’s really
we created was like a pressure cooker that that people walk into an elevator filled with camera people and investors and the literal pressure of rising through the building, running out of time, builds and climaxes. And when they get done, they either are really proud of how they represented their ideas and or they’re disappointed with how they perform. But we’re just giving them an opportunity to to do something novel, to sharpen a
that goes unused by a lot of us in most of our day-to-day lives, and that is how do start strong? How do you grab attention? How do you hold it? And how do you do that with non-captive audiences? ⁓ And so we’re doing that, ⁓ and we’re trying to make that a new way of communicating for founders. ⁓ Because it’s probably one of the most important skill sets that a founder can have ⁓ all the time, really. But in the information economy, it’s the most
important skill they might have is the ability to garner attention and especially to do so with limited resources. So we help them try to get along that path. We teach them how to do this. We hold open workshops so they can understand what the thought process is, what we want to get out of them, how they can best position themselves to succeed. And we’re making content with them and for them. ⁓ hopefully, fingers crossed, when this posts in February, we’ll have ⁓
reached over five million impressions and people will be talking about us all over the city of Boston. Yeah.
Keith Cline (07:18)
Wow, that’s amazing. And the content
is well, it’s very professional, well done, very current. How are you creating it? Because I just know what it takes to get a one minute video. It’s so much work. So ⁓ how are you going about getting the content done?
Rob Hughes (07:30)
Yeah.
Yeah, so we, it’s kind of a two, there’s multiple parts to it. One, let’s say there’s a strategy around what you’re gonna film, which is really always evolving. If you looked at how we film things at the beginning of year in Austin and how we film things at the end of the year Miami, there was a big evolution as we realized the things that we really wanted. And then as far as like editing and content, like you’re looking at it. Like I do most of the video editing on my phone. I take this little thing here, this little black box, and I put a,
I into CapCut, I download the footage, I cut it up, I send it to Gavin over at Corporate Dudes. He tells me how bad it is, and then I cut it back up and I send it back to him. He tells me how much worse it’s gotten since then. And then we go through this iterative process and ⁓ slowly we become a little bit more… ⁓
I’m at telling those stories. I have ⁓ a guy on our team, Barat, who helps me extraordinarily with these now too. And we just like sit down and we’ll just edit up stories for several hours together, just bouncing things off each other. We’ll show each other, here’s what I did. And then I’ll say, I don’t like that, change this. He’ll do the same thing to me. And we’re really, what we want to have is like pieces that founders can be proud of. Can we tell…
Can we compact like each one of these is basically three, three minutes of raw footage for each founder. Can we get that down to 40 seconds and can we bring an audience that’s swiping through the, know, and seeing all this stuff on their feed. Can we break through like, what is that and get their attention, hold it and have them have some sort of takeaway about who this founder is. We collab with them. We put their websites in the description. We’re hoping to make a big impact on their business. And as this thing grows, it will as our audience grows.
they’re going to have access to audience in a way that just doesn’t exist currently in the ecosystem. So ⁓ we’re pretty pumped about it actually.
Keith Cline (09:26)
Well, you mentioned that you have a unique perspective when it comes to hearing entrepreneurs pitch their companies because of the number of companies that you’ve heard and worked with through the years. So what are those common mistakes that people should really, really hone in on?
Rob Hughes (09:35)
.
I mean…
The number one thing I think is taken for granted is the beginning. ⁓ You really have to start strong. Our attention spans are getting shorter and shorter and shorter, and we’re not doing anything to reverse this, so the likely outcome is that the ability to garner attention is going to become even harder in the future. So starting strong, having a really like compelling statement, seven words or less that just boom, I’m here. Here’s what I’m doing.
and compelling, it doesn’t have to actually be accurate, which is one thing I think founders struggle with. It needs to be kind of a hook, a verbal hook to get the conversation started. And then from there, what are you doing? Why does it matter? And where do I fit in? And if you get those four parts of the pitch,
guaranteed you’re gonna have a much better outcome. And the best part is you can do that in less than 10 seconds. That whole thing can get covered in 10 to 15 seconds regularly. And I know this because I cut up all these pitches that are like 35 seconds of raw and I gotta get them down to 12 seconds, right? I 12 to 15, if they’re doing a lot, I gotta get down to 15. And most of the time when I’m doing it, I’m finding now that I’m…
growing into this, I’ve seen more elevator pitches than anybody and I’ve definitely edited more than anybody, you could kind of like reorganize the pitch and I’m like, wow, they have a great line that should have been at the beginning of the pitch that I’m gonna put in the beginning. And then I’m gonna reorganize the pitch around that. What, why, where do I fit in?
The biggest mistake that we see in the elevator are founders trying to fit too much information into the timeframe. Like I have 30 seconds, how much information can I fit in there? And it’s like, that is a complete error. The other thing is they’ll get into how. Like this is how we do it. It’s like, who cares?
Nobody cares about how the sausage gets made in the first 20 seconds. We want to eat the sausage. You can tell us in due diligence how the sausage works. If we have a 10-minute conversation, we can get into all the nerdy things that make you the best founder for this because you care so much about it. You’ve absolutely nerded out on this idea and this concept and you’re building this technology. Amazing. Let that come later. You need to get buy-in from your audience and you don’t start with how. You start with what and why.
Keith Cline (11:32)
Mm-hmm.
That’s great, great, great feedback. All right, let’s rewind the clock. So where did you grow up? What were you like as a child?
Rob Hughes (12:05)
Yeah.
Oh wow, I grew up in a little town called Kinston, North Carolina. My dad was in the Air Force. He was originally from New England, from Newport. My mom was from Sinsbury, Connecticut. They married and moved down to Biloxi, Mississippi, in the Air Force. And then I was born not long after they moved to North Carolina. I spent the first 12 years of my life there. So I moved up to New England on my 12th birthday. I got in the car, mom drove me and my sister
up. My dad and my brother were already up in New England and so that’s where I grew up. What was I like as a child? ⁓ Probably a very emerging version of who I am today which is a big personality. ⁓ I do recall my dad saying don’t say that and ⁓ my mom always saying don’t laugh at him to my siblings. ⁓ Don’t encourage him.
Because I’ve just always had a very weird way of seeing the world and then I articulate that in a an uncommon way that often causes a little bit of a giggle Yeah
Keith Cline (13:00)
Hahaha
All right,
so you studied architecture.
Rob Hughes (13:14)
Yeah.
Yeah, went worth here in Boston. ⁓ We was a great program. ⁓ I never practiced for one day because I graduated during the Great Recession when they were laying off all the architects. But ⁓ what I’m one of I think there’s a lot of reform that needs to happen in the education system. One thing I would say is if you want to learn a bunch of skills that you can apply in a broad range of professions, architecture is probably one of the best ones for doing that. You know, it’s you have to have a lot
of
different skills that you bring together, ⁓ both as a designer, an ⁓ orator, as a graphic designer. There’s a lot that goes into it. And then being able to distill good, constructive feedback from feedback that doesn’t actually apply because maybe you didn’t say something correctly. So it was a great ⁓ learning time for me. I don’t think I culturally fit in with the architects, and any of my classmates that went to school with me would tell you that I probably
had a hard time fitting in where it’s a very culturally it’s a very like humble you know don’t pound your test like be very like ⁓ I hope this is good and I was like I love this like I absolutely rock this design like this is awesome and like you can’t say that like well but if I think it why can’t I say it and so culturally I always had trouble you know making it through ⁓ those semesters but I learned a ton and it was really informative to like me working with
Keith Cline (14:29)
You
You
Rob Hughes (14:44)
I had a lot of empathy from day one because I knew what it was like to be given a problem statement and to make something from nothing and then present it to people who knew that thing better than you. It’s like, this is great. And like in a sleep deprived state with a lot on the line, 50 % of the people I started off my undergrad in did not finish. They either changed majors or failed out. And it was a very hard program to get through. And so the attrition rate was there.
the risk was there for all of us and we felt it so the pressure was very real in those moments and I think you know one wrong word and they just crucify you for it just absolutely eviscerate you like you said this like I didn’t mean it I’m tired that you didn’t mean it you wouldn’t have said if you didn’t mean it and you’re like my god my whole crit just fell apart create his critique well so they would bring in professional
architects that were practicing that had built buildings that we went through like, I love that building. And you did that? Like, yes. And then they would tell you in your sleep deprived amateur state, you’re still learning the art, how bad you were. And I never went through one crit that we didn’t have at least one person cry.
⁓ It was just normal. And so it was a very cool way for me to learn and to grow. I think going from there into entrepreneurship and working with entrepreneurs several years later, was just a natural, it was very natural for me, Vic. I get it. Like I have so much empathy for the thing that you’re doing and what you’re going through right now. That it was really, it made me a natural in it actually.
Keith Cline (16:18)
Alright, so how’d you get your career
started?
Rob Hughes (16:21)
So graduated, they were laying off all the architects, like I said. ⁓ I was selling shoes at Sports Authority and… ⁓
my trying to get a job applying everywhere, ⁓ hundreds and hundreds of applications. got, I get an interview now and then, but it was just not going anywhere. My parents and family sat me down. like, you gotta try something else. You’re good at selling. Why don’t you go do sales? Got a job at New York Life Insurance and was ⁓ gonna go do that, but I was deathly afraid of the phone. ⁓
just could not make a phone call to save my life. Just horrified of the thought. So I got a job at Scott’s Lawn Service doing door-to-door sales and cold calling for two or three, I think it was like two or three months. And did that drive the fear out of me, Keith? Like, oh my God, I was 300, oh yeah, 300 cold calls a day. Yeah, before robo-dialers, you just dial it. So you had like 50 minutes on, 10 minutes off of every hour.
Keith Cline (17:11)
Door to door, yeah. That’s legit.
Rob Hughes (17:22)
It was halftime after 40 hours. There was no windows in the building. It was a cinder block building. And then as soon as it was warm enough to go out and sell, we were doing door-to-door sales. There was still snow on the ground. you know…
It was brutal. you had a bad week, you were the low score, you weren’t there next week. So it was, again, another pressure cooker. You guys are seeing what I’m doing here. Like, I love pressure. think pressure makes dust and it makes diamonds and everything else I have no interest in. So yeah, I did well enough at it and then transitioned over to life insurance. So I ever knew life, New York life and was doing that for a little while. I hated the sales process. I got to be honest, learned a lot there, but I just
hated the sales process. It was terrible ⁓ for me because it had a lot of moving parts that… ⁓
just I’m not really great at some of those things. And so I ended up getting a job at Santander. They were hiring licensed bankers. ⁓ I started in Brookline working as a financial specialist and it was like their top tier clients. ⁓ And day one I was just like, okay, I love this. Like I’m really good at this. And so that started me down the banking path. ⁓ Met some people there. Banking is a small world. If you do a good job and take care of people,
you and I helped out this young man Patrick Gogan ⁓ a lot and he didn’t last very long at Santander but he remembered me and a couple years later called me up and said I want you to come over to First Republic we have an opening for you and I just went for it, risked it all and went over there. I was managing a branch on Federal Street at First Republic. It was the worst one of the worst performing branches they had. ⁓
were like the bottom three. It had been flat for 10 years. They’d had 10 different managers come in.
So it was a revolving door. My predecessor who had been demoted was sitting there when I got in there and everyone said, you’re going to fail. And looked up two years later and I doubled the business in every metric and every category and caught the attention of leadership. And they’re like, Hey, we need somebody to build startup banking for the East Coast. It’s working on the West Coast. Would you want to do that? We know you’re working with a lot of startups. And I said, yeah, that’s like my dream job. So jumped in.
started, spent the, you know, my boss is amazing man, Todd Rassiger, unbelievable, unbelievable man, and great mentor. He’s like, I’m here for you. I got you like every step of the way. One week into the job, he got pulled to interim CEO for a company that we had acquired. ⁓ And he was gone. And I didn’t see him. I didn’t see him again for two years. ⁓ So it was great. And so I’ve seen him intermittently at most and he was like,
Keith Cline (20:10)
Hahaha
Rob Hughes (20:19)
He got back from that tour of duty and said, hey, what have you built? And we sat down and he was like, my God, you’ve built so many communities and so many initiatives that allow founders to engage with us. And you’ve built real relationships and networks here. This is incredible. I think you’re ready for some help. so.
Brought my good friend Kyle Gross in, who I met when he was over at Bostoninno. he would did a little stint at we work and, ⁓ and he joined me over at first Republic and, it was just up in till up until the right from there. It was incredible until the bank run, which was, you know, kind of a downer to be honest.
Keith Cline (20:54)
Kind of a downer. So what, like what,
I just don’t want people to assume that I know that they know what you are doing as a banker for startups. Like what were you providing them as far as services and consultation and.
Rob Hughes (21:04)
Yeah.
Yeah.
Yeah, it was a lot of consultation and connection really and some community building, which I did in a number of different scales, but ⁓ banking is a commodity and it’s almost and if you’re in a bank that’s doing it for startups, they’re almost certainly not charging you fees. So you got to win somewhere and we didn’t have any lending capabilities that first Republic and we were trying to take a bite out of the SVB Apple and we did that successfully by being, you know, providing extraordinary service to our clients.
and then being really the connective tissue for a lot of them to not only other founders but other advisors and investors. So I did a lot of introductions. I hosted a lot of events, a lot of dinners, a lot of happy hours. I had book clubs and tequila clubs and pitch nights and AI. I had a fam founders in AI and machine learning which turned into like a showcase for founders and other AI founders would tear them apart. This is before AI.
the tail end of AI being cool the last time ⁓ before this new hype cycle. was great and ⁓ did a lot of things like that and ⁓ developed a good reputation for being very helpful and honest with founders. People end up doing business with people they like. It’s just what it is.
Keith Cline (22:27)
Well, I thought that was interesting, your founders in AI and ML. Because yeah, I think you started in 2018. So yeah, it was before the chat GPT moment. So what led you down the path of focusing on that sector?
Rob Hughes (22:34)
Yeah.
Yeah.
⁓ I was interested in it and I had a high concentration, ⁓ a higher concentration of clients that were there and friends that were in the space. So was like, I think this is like.
I liked the technology. thought that we had a lot of cross vertical qualities that would give me a lot of ability to go, you know, health tech, FinTech, know, normal B2B SaaS, B2C SaaS. all of it was starting, a lot of them were starting to use AI and was like, a lot of them at that time were saying like, oh yeah, we use AI or dot AI. And so it wasn’t as prevalent as today, but there was a thread there that you could pull on like, oh, are you
Are you using AI in your company? And they’re like, yes, it’s like our core thing. It’s like great, should join this group. I had a bunch of friends at MIT. My good friend Paul Cheek, was the co-chair of the Martin Trust Center up until recently when he wrote a book and became too famous, so he had to go around the world. Poor Paul. He was one of those founders that was initial to that group and invited a bunch of people from MIT. And before you knew it, we were doing monthly get togethers,
Keith Cline (23:39)
Ha ha ha ha.
Rob Hughes (23:49)
40,
50 people getting together sharing ideas, technology, how they did it. VC firms started hosting us in their offices, co-working spaces. We were just sort of brought it around the city on a little bit of a tour. There’s another theme happening here. I don’t know if you guys are noticing. And so we built a nice community. then again, COVID hit and it was like, boom, lights out. Did a couple of virtual ones and I…
Keith Cline (24:05)
Mm-hmm.
⁓
Rob Hughes (24:14)
I just like, it wasn’t it. I was like, I’m not gonna do it if it’s not it. So yeah, I might revamp it once it cools off. It’s just too hot of a space, you know? It’s like everybody would qualify and like I’m not qualified to know who should be in the room. So we’ll reignite it because I had some incredible, incredible conversations with some people that I will certainly hold in high regard for the rest of my life. So yeah, it was a great little initiative.
Keith Cline (24:26)
Right?
Alright, so back in the career, your professional journey, so you mentioned the bank run, so ⁓ JP Morgan ended up acquiring your bank, right? So, and then from there you moved to Citizens Private Bank?
Rob Hughes (24:50)
Yeah. Yeah.
Yep. So the JP Morgan thing was interesting. ⁓ I we woke up, I woke up the morning of, you know, after we, you know, that Monday morning, I forget the date. And we knew we were going to acquired that weekend, or at least we were hoping we were. That was the rumor.
And we just didn’t want to go through another bank run day. Cause it, you know, I don’t know if you remember there was an initial time period where it happened. I think it was like March 10th or whatever. And then it was like 60 days or something. And then it happened again on a Friday. ⁓ And.
We just didn’t want to go through that again. It was just going to be too much. And so I woke up really early, like four or five, like probably four in the morning. And I just saw, okay, JP Morgan had acquired us. There were a couple other buyers that we thought would have been better landing spots for all of us. And I had an inkling, like that’s probably not going to be for me, like a 365,000 person.
bank, I have long hair and a beard and I wear sneakers and jeans. Like, I swear a lot. The likelihood that I was going to be a good cultural fit inside of that organization was slim to none. So I kind of posted in the morning and then went to the gym. I had a post ready to go out on LinkedIn that was basically like, this is a great memory, like looking forward to whatever’s next. Kind of ambiguous actually. And I had so many calls that people like, take that down. You don’t want them to see it. was like,
I’m a free agent, like…
I don’t care if they see it. I’m glad they see it. I haven’t looked for another job. I’ve rebutted the offers of our organizations and not even had any calls. I had people in my life, great friends, like, need to be interviewing other places during that sort of period between the first and second run. And I was like, no, I’m going to ride this thing all the way down. I’m going down with the ship. I love this place. And I really didn’t have any conversations until it was
And then I was like, okay, I’m a free agent and started making some phone calls and having talks with banks, non-banks, lots of institutions that had offer letters from half dozen places. And by the time JP Morgan got to me, I had a half dozen offer letters. And I said, look, if you want me, give me your best and final offer, because I’m evaluating offers. And they were like, what are you talking about? I was like, what do you mean, what am I talking about? Like you work here. I was like, no, I don’t.
Keith Cline (27:16)
gonna that.
Rob Hughes (27:20)
I used to work here, like you need to acquire me, like you need to treat me like somebody you’re trying to woo. And they put like a pretty decent offer together, but it felt like a coast and lift kind of offer, like great title, money was good, but it felt like a settle for me, and I had too much piss and vinegar left in me.
Um, to, do that at that time. And I still do obviously. And I was like, I can’t do this. And so, uh, I had some great friends that had moved over to citizens or making the move. And I were like, you know, they didn’t tell me where they were going. Like, hold on, hold on. can’t say anything. And then, um, they, called me up and were like, Hey, come on over and help us start, launch the private bank. Um, and I, I brought, you know, Kyle with me and Louie and we went over and we’re starting, it started, you know, going.
ahead. And that was that was going fine. It was it was OK. was good people. Good organization. Rhode Island. You know, not bad. A lot closer headquarters than SF. And then I just sort of ⁓ I had I had this feeling from the very beginning that, you this wasn’t going to be forever. Wasn’t going to be my forever spot. Had an encounter with a social influencer named Simon Squibb. ⁓ Gave me a book called What’s Your Dream?
and I read it, took it to heart, and ⁓ we had planned on a collaboration together that ended up not panning out, but it was a great catalyst for me making that decision to make the jump. It got me in a mindset of like, do I monetize my network? And my friend Kyle Brockett called me up earlier this year and said, hey, I’m getting out of banking and I don’t know what to do.
And I said, okay, well you, you’ve been had run this program at first Republic called capital map, connecting companies with non-bank lenders. And then I’d sent him like a half dozen deals in the last month and he was helping those clients out. And I was like, why don’t we just do that? Like we could probably, let’s make that a company.
And so we launched Koo Capital and, ⁓ I quit my job very publicly on Tik TOK.
just made a post and said, hey, I’m done. And the bank called me up and said, what do you, you gotta take that down. I was like, I’m not taking it down. Like, what do mean? I was like, I’m done. I love you guys, but I gotta go try this. So been hacking away at that for the last eight or nine months. And we’re starting to, we’re winning deals, deals are closing. We’re starting to get paid and we’re conceived like.
Keith Cline (29:42)
Ha ha ha ha ha.
Rob Hughes (29:57)
that we have a great model, or have a really good reputation. We’re working with awesome clients and awesome lenders. And I’m having the time of my life building an incredible business with two of my best friends. And again, the learning from this has been so incredible. It’s such a raw experience. I’m learning every day. I’m growing. And I think most importantly, Keith, is like, I’m…
I’m actually being myself, which is really refreshing. Like there’s not like, ⁓ I don’t have to appeal to anybody’s approval. Like I, I don’t really care what people think. Like I’m just going to be me and I’ll live with the consequences of that. And I’m happy with who I am and who I’m becoming. And, ⁓ it’s, it’s, it’s been the most rewarding.
⁓ time of my life has been in the last this past year and that the oddest thing and I know I’m going on I’m a yapper that’s my kids call me yap Jesus not tech Jesus they say yap Jesus you’re yapping again but the most rewarding
the most interesting thing is the beginning last year I do one New Year’s resolution I haven’t picked one out for next year I’ll pick it next week but I always keep just one New Year’s resolution just one I want to nail one thing because if you do two or three you’re not going to do them or at least I won’t
And mine for this last year was like reduce regret in your life by 50%. And it was just like, man, did I nail that one.
⁓ I’m coming out of this path this year going I don’t really have any any regrets I I have a lot of new skills I’ve acquired I’ve got a lot of growth that I can exhibit I have a lot of proof points that to myself and that I’m I’m on the right path ⁓ and I just don’t have a lot of regrets I don’t have a lot of past regrets I have a lot of gratitude for
my experience so far and a lot of expectation around where the path is going to take me and ⁓ it’s just been an incredible incredible year.
Keith Cline (31:59)
So, Koo Capital, what do you guys do?
Rob Hughes (32:00)
Yeah.
We do ⁓ private credit advisory for growing companies and emerging projects. So you have a capital need, sometimes that’s equity and sometimes that’s debt. And if it’s debt, we help you find the right lender that can give you fair terms and help you accomplish your goals. make those introductions and advise those clients around their strategy, their engagement and their choice of which lender they go with.
And the awesome thing is we have to pick who we work with. And I am proud to say we’ve done exactly zero outbound. And we are.
busy every single day, meeting with new companies, new projects and new lenders and really building something that’s allowing founders to keep more of their equity and keep growing at the same time. So it’s a lot of fun. I’m learning a lot too. I didn’t think mining, I didn’t think I was gonna learn about mining in 2025. I’ve learned a lot about mining. Like I didn’t know what an off take agreement was. Like I was like, what is that? know, LOI for
mining, what in the world, ⁓ who’s Umacore? So it’s been a really great, it’s been a really cool experience so far. But yeah, we’re having lot of fun working with some great companies and projects and learning a lot.
Keith Cline (33:24)
So it’s a vehicle that I don’t think, you know, it’s always like raising venture capital. That’s always the mindset of entrepreneurs and kind of what they’re trained to think about. But they’re all alternatives like what you’re providing. So what are some of the things that entrepreneurs should be thinking about as they’re looking to fund their company?
Rob Hughes (33:30)
Mm-hmm. Mm-hmm.
Thank
Yeah, I mean, there’s a time and place for every financial instrument and there’s not one solution that’s right for everybody. And so ⁓ when you’re looking at your business and if it is actually a business, excuse me, what I mean by that is like, hey, is there a historical data to support that you’re on the right path and you’re the right team to execute? And that’s usually financial data. Like, hey, we have this much in sales, this much in inventory, this much in collateral. ⁓ maybe going out and diluting yourself a ton doesn’t
make a lot of sense when you could put a facility in place or maybe supplement an equity round and get tax and debt on top of it and really give yourself a big opportunity to win a larger window. I would say a lot of times like we try to be as transparent as we can with clients and prospects so they’ll come to us and say, hey, you know, I raised this round like who’s your lead investor? And if it’s like an A plus investor, like you don’t need us like go.
just ask them to introduce you, their bank will probably give you incredible terms. But if that’s not the case, and that’s most of the companies, by the way, then maybe you don’t want to just rely on chat GBT and trying to email an info at, or try to search out the best contact you can find. ⁓ Maybe you should have someone that ⁓ knows these people personally, that knows what they’re looking for and can help guide you along that journey. ⁓
of things we’ve realized that we weren’t so obvious was that a debt pitch is a lot different than an equity pitch. And founders, when they’re on the equity trail and their investors are wanting to see promise and opportunity and upside, and they’re good at pitching that, and then they get into a debt conversation and they’re doing that. And the lenders are like, my God, please stop. Like, want to know nothing about opportunity. I want to know about the risk. Where is the risk? What would cause your business
Keith Cline (35:35)
Mm-hmm.
Rob Hughes (35:38)
to
go under and if it does and you’re unable to pay the loan, how do I get made whole? And those are completely different positions. so helping founders refine that story, walking them through that, giving them the script, here you go, take the script, read this, read it. That’s been an incredible learning experience for us as well. And like saying, hey, this is what needs to happen. Here’s the things that matter to this type of investor. And they are investors in a way. And so like,
Keith Cline (35:55)
You
Rob Hughes (36:08)
able to speak to them and meet them where they are. It’s a lot of fun. I didn’t know as a deal dog, I, god damn it, I love it. I have a blast.
Keith Cline (36:17)
So what are the qualifications that you’re looking for on both sides? You’ve got lenders, you’ve got borrowers, what do you typically look for?
Rob Hughes (36:25)
Yeah.
So the lenders is kind of interesting because you meet them through a very array of different ways, generally through our network. So lenders do business with a lot of the same lenders. And so they’ll introduce us to their friends. They’ll say, you should talk to Joe over at this shop. They would love this. Let me introduce you. You strike up a relationship with Joe. You build out their buy box. What do they like? What do they not like? What kind of collateral are they looking for? What kind of metrics are they looking for? Minimums, maximums, types of loan facilities they do.
kind of get into it, start understanding what they’re, you know, what they’re looking for in the next quarter. Like what kind of deals do you want? Are you looking for robotics? Are you looking for SaaS? You’re looking for AI. What are you looking for? Are you looking for CPG? Like what’s going on? And what kind of metrics do you want to see for those two verticals? And so that’s on the lender side. You just kind of accumulate those over time and then you have to build those relationships. So I spend a lot of my time talking to lenders and saying, you know, what do think of this deal? How did that call?
go? What are you thinking about this? What didn’t you like about it? Going through the financials, what’s good, what’s not? Why didn’t you like that? And then on the other side, on the founder side, it’s just you got to figure out whether it’s a good credit or not. You know, it’s like, what’s the, you have to put your credit hat on and be like, okay.
What’s the risk in this deal and how much no one comes to us unless there’s hair on the deal, how much hair is on the deal and can we get the shears out and give it a haircut? I know that’s ironic coming from me or there’s just a little too much hair. ⁓ so figuring that out. Also, do we have the lenders that in our network that could do this deal would want to see this deal? And if not, do we think we could acquire them quickly enough to match up with the timeline of the borrower? And so it all kind of goes into a
a nice mix of weighing out the positives and negatives of every opportunity together and figuring out which ones we want to spend our time on. Yeah.
Keith Cline (38:24)
What have you learned so far in a short window of time of running your own company?
Rob Hughes (38:31)
You gotta be in the boat with people you trust 100 % and you need to be able to communicate very, very clearly and honestly and directly with them what you’re seeing, what you’re doing and why. And they need to be able to do the same thing with you. if you can’t do that, it’s gonna be really hard to innovate well together, especially at speed.
⁓ That’s probably the biggest thing. The other thing is no matter how you’re feeling, you just got to get it done. ⁓ I have moments of triumph and moments of defeat that if I stand in the sun too long or in the rain too long, we’re dead. No matter how I’m feeling, up, down, in between, I just have to get the work done. ⁓ so feel those things for sure, but get the work done. ⁓
via success compounds and so does failure. So if something’s not working, let it go. Especially if there’s a lot of evidence to support that, that’s not it. And if it is working, double down. Our business model, our audience that we were seeking has changed a couple of times since we started this process.
⁓ You gotta be okay with that. Like, hey, we’re finding product market fit. We’re finding the client types that we enjoy working with the most, the industries that we have some special advantage in that we can bring to the market. And you just kind of like in our mode for getting paid and keeping the lights on and how we wanna build this business and our brand. it’s a lot of fun. We just did like our…
you know, annual recap yesterday. So a lot of this is fresh in my mind, but it’s a, it’s a lot of fun to have those conversations instead of like, what’s your fun fact? You know, like, please, if I please, no, I don’t want to talk about my fun factor. Like, you know, I, we’ve got to run this up the flagpole to see if, you know, we can get approval for it. It’s like, Oh my God, what approval for what? Um, so I I’m definitely in my
in my element where I’m able to make decisions and act on them and ⁓ own them. So it’s been.
It’s been good. I think the biggest learning is like, I’m made for this. You know, was the fact that I was an employee for so long. Congratulations to Todd Rastiger and Sam Heshmati for convincing me to be an employee for as long as they did, because they did God’s work. Because I was not meant to be an employee. Like very obviously, I had hundreds and hundreds of founders telling me, you should not be working for anybody. You are an entrepreneur through and through. And I was like, I’ll do it when I’m ready. so, yeah, good. God bless those two gentlemen.
They’re wonderful people. ⁓ But yeah, it’s really cool to realize like, you’re actually built for this. Like you’re good at this. You can deal with it.
Keith Cline (41:28)
So what’s going on in the Boston tech ecosystem? You’ve got a strong pulse on what’s happening, so what’s the latest?
Rob Hughes (41:36)
Wow.
Yeah, I think it’s ready to come back. I mean, we’ve been coming back in little fits and spurts and people are starting to come back together. We were probably the last major city to come out of COVID, truly come out of COVID and get back together and start coming together in person. And I feel like it’s almost back to where it was from an ecosystem play. I mean, we’re bringing the PitchLift back to Boston for a reason.
We think there’s a hole there that needs to be filled. And that hole is called fun. ⁓ There’s nothing fun happening. If it is fun, it’s just fun and there’s no real value. So it’s like either really learning based and serious or just fun. And we’re like, why can’t we have both? Why can’t you have a blast learning a new skill, meeting new people?
interacting with investors and making incredible content and memories that you’ll never forget. ⁓ So that’s we’re bringing the PitchLift back and we’re doing it simply because
Well, there’s a number of reasons, but one of reasons we saw the opportunities, like there’s a gaping hole in the market for this. There’s so many people here building companies and the thing they need access to is eyeballs and we can give them that. So let’s build a media company and a show that allows founders to come on and do their best and have a blast, meet new people and learn a new skill. Yeah.
Keith Cline (43:03)
Yeah, I agree. Boston
needs more. ⁓ It got sleepy and it’s been coming out of its dream and finally becoming more alive. And yeah, we need more fun events like PitchLift and others. ⁓ that is good stuff. All right, three apps you can’t live without. can’t… Dinner? Yeah. Wait.
Rob Hughes (43:19)
The dinners, one second, second. The dinners
are important. Like dinners are super important. You gotta have them. A lot gets done over dinners. Somebody else can do the dinners.
Keith Cline (43:26)
Okay.
Rob Hughes (43:31)
I’m not going to do the dinner. It’s like, want to do the, I want to do this, you know, I want to do this thing that like people like, I can’t believe I just did this. I want to give you something to talk about in your khaki gingham life. When you go to Christmas dinner or New Year’s and you’re like, what did you do? It’s like, I was in an elevator with a camera crew and a venture capitalist. Let me show you it’s here, you know, on Instagram. So that’s sort of the vibe is like, let’s bring, let’s give Boston needs a little fun injected into the system. They need a little bit of, and something to talk about, baby.
Keith Cline (43:33)
Yeah, I don’t…
Yeah.
Yes,
yes. Stop being so humble and just like reserved. It’s like, come on people. ⁓ I laughed at the dinner thing because I’m like, I just don’t like it was like, OK, you’ve got the obligatory picture on LinkedIn of everybody sitting there like looking at the. I’m like, there’s so many of them, too. I’m like, are these working? And I think they do work for a certain set, you know, but you can’t really scale.
Rob Hughes (44:01)
You know? Yeah.
God, those pictures are bad.
They do.
Keith Cline (44:28)
dinners like that where it’s like, you know, they’re all sitting next to each other and you’re supposed to engage in conversation. I don’t know, I just, I’ve never gone that route and it would be a logical thing, I guess, for me to do as, you know, a community builder myself, but I just, don’t, I’d rather do other things.
Rob Hughes (44:46)
I’d rather be home having dinner with my family and I don’t even eat dinner. So it’s like, I’ve intermittent fast. Like I’d rather be at home hungry than hungry at a table full of people. And I’ve done my first year dinners. I’ve seen the marvelous things that come out of them. I know how effective they are. just, I want what all men want, more.
Keith Cline (44:49)
Right.
Rob Hughes (45:08)
I want more, I wanna do something fun and I wanna have a bigger impact than seven people at a time talking around the table in two minute segments about the thing they’re working on and blah, blah, blah. It’s the personification of medium talk. It’s like, ugh, can we get a little better? And some of them do it and some of them don’t, but whatever it is, I’m glad they exist and I’m glad I’m not the one hosting them.
Keith Cline (45:38)
There you go. All right, three apps you can’t live without. It can’t be Slack, email, or calendar.
Rob Hughes (45:38)
Hahaha!
Oh wow, that’s a great question. Cap cut, oh my god, I have to have cap cut. This is gonna sound terrible. All these are gonna sound terrible to people because they don’t know the world I’m living in, but I gotta get into Spotify. I have to have Spotify on. My rap was mildly depressing because I was 64, 74, 74 years old. I am not 74. I am at least 52, no.
And then, I said CapCut, this is gonna sound terrible, but I would have to say Instagram. Like I am learning the art of that algorithm. I am understanding the slope of viewership. I am learning the sweet, sweet science of how to get into people’s feed and how to stay there. Excuse me, and that is bordering on an obsession right now. And so I have to ingest a lot of.
things to get to understand what works and what doesn’t. I have to try a bunch of things.
I didn’t know what a trial reel was. ⁓ I had no idea how to make video content. ⁓ you can do a trial reel. You can go on and like make a reel for Instagram and you could put a little button on there. Just click and it says trial reel and it sends it out to not your followers. So everybody’s not your follower. You can see like what’s the engagement like? Do people stop and watch? Do they share it? Do they like it?
Keith Cline (46:48)
What is it?
Rob Hughes (47:08)
Do they ignore it? Do people just pass on by it? And if they keep passing on by it, don’t post it. why, nobody wants to, nobody wants to post stuff that nobody views. So it kind of gives you ⁓ a, like a soft open for a post. Like, is this good or not? And again, the general audience is like the thing that’s really telling. I’ve spent a lot of time on TikTok this year. I have not figured out that algorithm, but gosh, I’m going to get it eventually. And that is just the purest form of attention grabbing behavior. Are you able to grab attention?
If you could do it on TikTok, you can do it anywhere. It is so difficult. But same principles. They do not have a trial that I know of. If they do, I’ll start using it. But yeah, all these platforms do a really great job of helping people who are creators, which apparently I am now. ⁓ I am a creator. I’m a content creator. And I’m gonna be great at it. The understanding where you’re losing audience, second by second, Keith. I lost him at two seconds. I lost him at three seconds. I lost him at four seconds.
And there’s ideal slopes or ideal curves. And then there are like death curves. And then there are like the curves that everybody wants, which look like that. You it’s like you just lose a little. And the difference between your content getting to 200 people and 2 million people is not that big. It’s not that big. It’s crazy. ⁓ So learning that is as made Instagram.
Gut to my bottom four along with CapCut and Spotify.
Keith Cline (48:38)
Okay, is the length of video 12 seconds your desired length?
Rob Hughes (48:40)
Yeah.
So there’s a lot of, I mean there’s obviously advantages to doing short video. Because one of the most important metrics is how many people finish the video and how many people start it over. Do they watch it again? And so obviously if you do this on a very hyperbolic version of this, you have a two second video, the likelihood that somebody will make it through and come back around very high versus a two hour video, very low. In that, you kind of have to figure out where you want to play.
Gavin, again, I’m gonna mention him, one of the founders over at Corporate Dudes, has been relentless on me of cutting me down from minutes upon minutes to seconds. And it’s hard. I can do 20 seconds, I can do 10 seconds, can do, I know how to get there. just, you know, it’s just what am I trying to get done in this post? What am I trying to do? And there’s no real…
rule around time domain except unless you’re a known entity, never go beyond 40 seconds. Nobody’s gonna watch. You won’t make it. Yeah. Yeah.
Keith Cline (49:47)
That’s good, good advice. All right, how
about a podcast or book recommendation for entrepreneurs?
Rob Hughes (49:54)
Man, I think for books. think shoe dog is one of the best entrepreneurial books I’ve ever read. ⁓ I Think it’s fantastic. It really shines a light on the journey ⁓ and of a founder building out and probably a More than more iconic companies in the world and how even that wasn’t very straightforward It was it was a convoluted very treacherous path for Phil Knight and for that brand and so I really enjoy that podcast
I have not been podding. I was a big podcaster for a while. ⁓ I don’t think I listened to any pods this year. Maybe a couple of ⁓ Joe Rogan experiences, because I was a big G-A-R-E guy, and if he has somebody good on, I’m going to listen to it. ⁓ Nope, I started a pod this year, but I don’t listen to pod.
The Double Stack Podcast, Formula One with me and Jason Fernand. It’s pretty good. That’s a great podcast. Everybody should check it out.
Keith Cline (50:55)
What’s your favorite pair of sneakers behind you?
Rob Hughes (50:59)
⁓ Probably these. ⁓ Those are really great. They get a lot, I mean all of them. I like all of them. I wear all of them. The baby blue ones David Horn gave them to me as a quick gift when I quit my job. So every time I think of them I get really happy. ⁓ They all have a little something something. I wear them all. I wear the crap out of them. Because I think sneakers are made to be worn. And they should have holes in the bottom by the time you throw them out.
Keith Cline (51:29)
Alright, what else do like to do for fun outside of work?
Rob Hughes (51:30)
Yeah.
Some crossfitters, I do that in the mornings, which is brutal and terrible. I mentioned I have a Formula One podcast with Jason, so I watch a bit of Formula One, get together with my friends over that. I have two lovely boys, Teddy and Bear, that are gonna get a lot of my attention after we wrap here. My lovely wife, Jessica, my family, a lot of my time. So between my work at KOO, me building PitchLift,
learning social media, cross-fitting, Formula One, and family, there’s not a lot of space. So my friends will tell you getting together with Rob has never been harder.
Keith Cline (52:15)
Cool, well let me get your time back so you can spend some time with your family. So, Rob, thanks so much for taking the time to walk us through your background story. Obviously all the great work you and your colleagues are up to at Koo Capital and obviously all the great advice.
Rob Hughes (52:21)
Yeah.
Awesome. Keith, you’re welcome to the pitch anytime. We’d love to have you. We think it’s a best experience live. You can come anytime and ride that elevator or watch the horror as founders turn away in angst and anxiety or puke into a bucket. And we’ve seen all those things, but it’s a once. It’s a very it’s a memorable moment for sure. So we’d love to have you ⁓ at one of our 12 shows in Boston in 2026.
Keith Cline (52:59)
Very cool.