Sam Pollaro is the Co-CEO of PicassoMD, a telehealth solution that instantly connects healthcare providers for clinical decision support, referrals and care coordination. Before PicassoMD, Sam was previously SVP of Strategic Initiatives at Kayak-OpenTable after that company acquired Venga, his last start-up. Sam’s first venture was an online flower subscription business that was acquired by Battery Ventures portfolio company HBloom. Prior to taking the entrepreneurial leap, Sam was a Principal at Portfolio Logic, a healthcare-focused investment company. Sam holds a BS in Mechanical Engineering from Carnegie Mellon. Sam is passionate about entrepreneurship, technology, and improving our healthcare system. A 3x entrepreneur himself, Sam is always willing to help other founders because he has been in their shoes.
Bryan Wish: Sam, welcome to the One Away Show.
Sam Pollaro: Thanks. Happy to be here.
Bryan Wish: Yeah. Good to have you. And it’s been good getting to know you and following your journey and super excited for this. So what is the one away moment that you want to share with us today?
Sam Pollaro: My one away moment was when I, for a period of about eight hours, stepped down from my position as CEO of my last company before regaining the helm a few hours later.
Bryan Wish: Wow. Okay. That is not what I was expecting, but I think that’s fantastic. So, well, let me ask you this, what company was it? And what propelled you to say, “I want to step away from this position.”
Sam Pollaro: Sure. The company was called Venga. We made software for the hospitality industry. And yeah. We launched in 2009, and we had a couple years of false starts. And we had retrenched and gone back into an accelerator after already launching the company, which is the backwards way of doing things. But we felt we had to do that to retrench. And things were still continuing to go sideways for the most part. And we had an investor approach us and said, “I want to invest, but I also want to be the CEO.” And for a brief minute I was struggling through a lot of stuff in my personal life as well. And for a brief moment, I thought that would be the best thing for the company is to bring in this capital infusion, let someone else take over the helm and move on to do something else.
Bryan Wish: Okay. Well, so you were going sideways. Things weren’t maybe as going humming along as you wanted. And this maybe scenario came in that maybe felt like would solve all remedies. You get a cash infusion. It would take you out of the leadership position, so you could focus on some things at home. I mean, I want to lean into that. When you were in that position, and sounds like you said, “I’m going to do this temporarily,” how are you weighing that decision? What was going through your mind? How do you look at it from a pro standpoint? How’d you look at it from a cons perspective? And I have to imagine too, a lot of internal grappling inside of what do I do.
Sam Pollaro: Yeah. And it’s hard because I was thinking about it what’s best for me and my family at the time. I had my son was, I think, one or two years old at the time. So I had a young family and all the stress and struggles that comes with that. And then there was the company and our investors, and I was thinking, well, what’s best from the company’s perspective? I’m just one person. So even though this isn’t what I want, is this best for the other employees of the company? Is this best for the investors of the company? Is this best for my business partner? So I was trying to figure out what’s best for me personally, what’s best for the company, and trying to weigh that against my own ambitions. And of course not being the way this… I never envisioned stepping aside or failing as an entrepreneur. So, that was the struggle that was going on.
Bryan Wish: Got it. And just for context, how long had you been building the company prior to this investor coming into your orbit?
Sam Pollaro: I think at that point it was probably a year and a half to two years. So not an insignificant amount of time to invest but, yeah, not 10 years either.
Bryan Wish: Right. Makes sense. So you had your son that you were survival, trying to make sure that you could feed, and feed the family. You were young, early into the company without a lot of, it sounds like, a ton of clear direction or paths. Feel free to share this or not share this. But if you don’t mind who was this person? And if you don’t, if you can’t share, no worries. You mentioned that you went to step down, but then you didn’t. So my question for you is what changed in this few-hour period or few-day period where you-
Sam Pollaro: Yeah. It’s actually interesting story. So it was the pitch day for the accelerator program that we were in. And we had been trying to raise money to really what we felt we needed to get us out of our funk and really start to grow the business. And this investor was coming in saying he wanted to run it. And we were preparing for the pitch day. And someone from the accelerator program also said, well, maybe it’d be interesting to let him pitch, this investor, just to bring a new face, someone that people haven’t already seen and a new dynamic. And so after a lot of thought, I said okay. We’ll let him pitch, and let him position himself as going to be leading this company going forward.
And so that was what happened. And the pitch was actually… it was, there was an afternoon session and the morning session. And during the morning session I said, “Okay, sure. You go up and pitch.” And he did. And his pitch, which just made it so obvious that his style, he was very… he bragged a lot. It was very about him. It was just very inconsistent with the values of our company. And so it was a lunch in between the morning session and the afternoon session. And in that time, I said, “Look, this is not the right decision. I need to step back into this role and continue to lead this company because I saw what briefly flashed in front of my eyes the future of this company under someone else’s leadership.”
Bryan Wish: Wow. And you saw that flash on a big stage. Right. Picturing your business, and you [crosstalk 00:06:15] like that. Being able to see that and acknowledge that, I mean, clearly it says you were very aware. I want to ask you a question. And if this is too personal, feel free not to answer it. But you considered giving this role up. You considered giving the vision of the company, just putting it in the hands of someone else, who clearly wasn’t a fit to do it. Did you believe in yourself at the time? And did you think your team believed in you as well?
Sam Pollaro: I don’t think that I had the conviction in myself that I should have had. And I think as entrepreneurs we always have some self-doubt. And I think what really pushed me over the edge was, I can deal with my own self-doubt, but I think was when the folks from the accelerator said, “Well, why don’t you give someone else a try? Maybe a fresh face would help.” That’s when it said, okay, well, it’s not just my self-doubt, but other people maybe believe that I’m not the right person for the job. And so that’s when it really, it was beyond just me. It was other people having the same thoughts. And that’s what pushed me over the edge to think about stepping down.
Bryan Wish: Wow. Okay. Well, I mean, I relate a lot to that. When you don’t always feel like you have the most people around you are equipped with the right skillsets, and all the hell and high water moments of surviving. So thanks for sharing. It must have been really hard for you at the time. I can’t imagine myself doing being in that, those shoes and having to decide. So you said, okay, you saw them pitch and you said, “This is not aligned with my values. I’ve worked too hard the last year and a half to give this away.” And you said, “Okay, I’m going to put myself back in the driver’s seat.” How did things change? How did things evolve?
Sam Pollaro: Actually it was great. So we pitched that in the afternoon session. Fortunately there was the investor, a seed fund here in the DC area, attended the afternoon session, where I pitched. Not the morning session. Ended up leading our series A round. We raised a million dollars series A round. And that was the catalyst that we needed to really start to grow the company. So we got the one investor that brought in some other investors. And that was all we needed to really get moving.
Bryan Wish: Got it. Makes so much sense. So you got the 1 million, and you raised the capital. How did you start to deploy it? You said it really got things turning and moving. But where did you start to see the most growth? And you said you’re in the middle of raising money right now, so I’m sure it’s skriking some old memories for you. Once you got that capital, how did things start to go? And what first deployed the capital, and start to see the changes?
Sam Pollaro: Yeah. So I talked about how during the first, when we first launched, we launched and then we had to pivot. And so we had to retrench. And so we really had to invest first in the product, and rebuilding a new product for the market that we had identified. And so that was the first step in hiring the engineers, and the team to do that. And then from there, bringing on the sales and business development folks. But as an entrepreneur, if you’re not your first salesperson, you’re doing something wrong. So you’ve got to be out there and sell, talking to customers and hearing what they want and what they need and, what, getting their reaction firsthand. So we use the money to bring on the engineering and product team we needed to complete the pivot.
Bryan Wish: Got it. I love what you said about being the person who I think I met you through. I was having a conversation with him recently and he said, “The entrepreneur, no matter how big the company is, is always the best salesperson.” So you realize that. But you had rejig the product you said. What about the product was maybe wrong for the market at hand? And then how did you bring it around to a place where you got it right for the customer profile that you were really trying to penetrate?
Sam Pollaro: Yeah. So we were trying initially to build a two-sided marketplace for the restaurant industry, where we would connect consumers with restaurants, and we would help consumers decide where to go out to eat. And we would help restaurants promote the things, the food, the events, the specials that they were doing in the restaurants. And that’s a really, really difficult business that those two-sided marketplaces, because you needed to always be balanced. You need to acquire consumers. You need to acquire businesses. And so it just takes a ton of capital. And it’s a very difficult market. And so what we pivoted to do is really focusing on the business in this case, the restaurants, and building a CRM, customer relationship management, platform for restaurants that would help them to keep track of and engage the customers that they already had, and help to bring them back more often. So, that was the pivot.
Bryan Wish: Super neat. I’m thinking about me just going to restaurants. I sometimes question why Chipotle or why whatever down the street doesn’t… I mean maybe they do. But it’s neat that you were able to say, “Let me go really acute. Let me just build CRM four restaurants.” Now, when you were building this, what were maybe some of the product adaptions or features or things that you were able to build just for the restaurant industry that really allowed for this product to start catching traction and getting on? And then once you started to see that, how did that maybe change your sales and marketing processes?
Sam Pollaro: Yeah. So-
Bryan Wish: And engineering.
Sam Pollaro: Good question. Sorry?
Bryan Wish: And engineering.
Sam Pollaro: Yeah. So the restaurant industry is a little bit unique in that the data systems they use don’t talk to each other. So when you go to a restaurant, if you make a reservation on OpenTable, or Resy you make a reservation, and so the restaurant knows who you are. They see reservation from Bryan Wish at 7:00 PM tonight. Then you go into the restaurant and you buy a bottle of wine, and you buy a steak and an appetizer. And all that data lives in a separate system. And those systems don’t talk to each other. So restaurants have no idea what their customers like to eat and drink, which is incredible because they always say the first rule of business is know your customers. And so here, the insight we realize is that restaurants have no ability to keep track of their customers and how often they come and how much they spend and what they like to eat and drink. But by connecting those two data sources, we are able to give restaurants the information that they need to make use of it and to really customize and personalize the experience and tailor their marketing and engagement towards individual’s actual preferences.
Bryan Wish: Yeah. Now I’m thinking of pre-COVID days, where you walk into a restaurant you’re regular at, and they just know your order right off the bat. And here you go. But how do you scale technology? Right. Super cool. So once you’re able to find that traction and restaurants saw this as valuable, what did you do on in the position of being CEO? Not giving it up. Saying, “Okay, this is how we need to go scale our sales processes.” Or how did marketing function differently? Or you evolve the product to equip yourself to scale with the software that you had built?
Sam Pollaro: Yeah. So a lot of it had to do with the relationships that we built and the channels and partnerships that we created. So we created a really strong partnership with OpenTable, who ultimately ended up being our acquirer. And so we were able to really leverage the footprint. And my co-founder actually is really to credit for this, but he built an incredible relationship with that organization, so that they were actually selling our products for us. And so they had the relationships with the customers. They already knew them. They were much more likely to pick up the phone when they called than if someone from Venga called, who they’d never heard of. But we were able to leverage that relationship to grow the business and eventually to be acquired.
Bryan Wish: So cool. Something, Sam, that I think is coming across is this just constant desire to turn over every rock, maybe feel your way through some decisions and do what’s right. When you do that, you have to make a lot of hard decisions along the way. And it sounds like this journey was met with a lot of persistence that you just and unwavering drive to figure it out. As you were navigating this pivot to traction to acquisition, maybe if you could lean into, what were some of the hardest parts where you really had to persevere and overcome things that maybe you just never thought were possible?
Sam Pollaro: Yeah. I always say building a business is always two steps forward and one step back. And as an entrepreneur you often take those one step back a lot harder than maybe even those two steps forward. And so every time you lose a customer, every time you lose an employee, every time that you release a version of the software that has a bug on it, you really feel it personally. And you feel it physically almost, in your body when something like that happens.
And so it’s very easy. Along the way you often get there’s other opportunities that come up, and people might reach out to you and offer you jobs. And so there’s a lot of opportunity to just say “You know what? Why am I dealing with the stress and headache of running this company when I could be sitting back and collecting a paycheck like everybody else. And going home and leaving my work at the office.” And so there were probably, I don’t know, half a dozen times when I thought about giving up along the way, just because the, it seemed, the challenges seem so insurmountable. But I’m so glad that I stuck it out at every single one of those intersections, because all it takes is one time where you decide to let it go and to give up. But you have to make that decision actively, multiple times 5, 10 times to actually stick with it, if you’re actually going to reach that the success at the end of the tunnel.
Bryan Wish: I relate so much to that, that losing a customer or that something going wrong with the product and how that just crushes you. And you do take it personally because it’s an embodiment of something you created. So makes sense. Within those 5 or 10 moments where you just bounce back, overcame insurmountable odds, as you put it, do any one or two of those just stick out that are worth sharing. I know you’re raising around, and you want an investor to know about one of those stories. What’s maybe one you would tell them?
Sam Pollaro: I mean, there was definitely a time when we were out of money and we were bouncing checks. And I forget there was some bill that we had that was supposed to be automatically paid every month, our utility bill or something. And every time the utility would try to take the money out of our account it would bounce. And then the bank would then charge us an overdraft fee. And so our balance kept getting lower and lower and lower. And you’re just watching it. And the first thing that we did anytime we got low in cash is my co-founder and I would stop collecting a salary. And then the next step is we have to put more money into the business.
And at some point you’re looking at your own personal bank account and your company’s bank account, and you’re seeing them both start to dwindle. And you’re just wondering how long can you keep this up? And, but every day you have to go in, and you have to put on a strong face for your customers and your employees and your investors, and you have to maintain that confidence. And it’s hard. It eats away at you. And having a good co-founder, who you really get along with, is so key. Because on some days your co-founder might be really down, you’ve got to pick them up. And then they’re going to do the same for you. And I was lucky to have an awesome co-founder, who was able to keep me motivated when I was feeling down. And I did the same for him.
Bryan Wish: That’s great. Yeah. It’s plus one on the co-founder, but I think you’re right. You got to keep showing them strong and being there, right, even when you don’t want to while your bank account is dwindling. So, Sam, take us to maybe some of the highs. It took a while to maybe get some of these traction points and momentum going, where you got to a point of acquisition. How do you get the business to a place where it was really solidified, a place where you felt like you could exit? And just maybe tell us more about that journey from nothing to really getting in somewhere after the race.
Sam Pollaro: Yeah. I mean, I remember when we signed our first real enterprise client, and realizing that how much Rev knew that deal was going to bring in and realizing, okay, this is, now we’re finally getting somewhere. And those wins. Because it’s not just about the revenue. But it also gives you reference-ability. So when you can say to sales prospects… oh one thing they’re always going to ask is who uses this? And so you if you can just get a couple name brand customers. And even in the beginning if you just need to give it away, don’t charge them. But that way you can say the best, whatever industry you’re in, uses this, uses our product. That makes it so much easier to then sell it to your second customer, and in third customer.
But I remember the feeling of we signed a couple large enterprise customers within a few months of each other. And that’s when I knew, Hey, this is actually working and the business growing, and we’re starting to make money. That’s always a huge win for me. And then the other thing that I really love is seeing the people that join the, our companies do well and succeed and get promoted and go from being in an entry-level position. We hired someone who… we originally hired him as an unpaid intern, and he worked so hard. He proved himself, and made it. And he was two years later, three years later, our director of operations and on our management team. And so seeing people succeed like that was always the most rewarding part of the business for me.
Bryan Wish: Yeah. I love that. I love the story of you empowering people. Maybe they don’t have the experience and could bring them up to a leadership level to own key parts of the business. Not easy to do, especially if someone’s green or they don’t have that experience. I was listening to a podcast this morning, actually with Ben Horowitz. And it was talked about actually in a software enterprise business bringing a salesperson, the key position, who’s never had sales experience in software is a really bad decision because you need someone with that experience. And you’re saying operation’s a little more behind the scenes, so that might be different. But you’re able to bring someone into a role and groom them. So I can relate to seeing that happen. And that’s also happened on my side with what we’re doing, with our head of operations is now my co-founder. So, thanks for sharing.
Sam Pollaro: Yeah. What we found, one of the rules that we lived with is we hire great people when we find them. And in my experience, great people will be great in almost any role that they do. And sure there might be a learning curve. But if you’ve got the passion, enthusiasm, the intellectual horsepower, you can succeed in a lot of roles. So when you find those people and you grab them even if you’re not hiring for any role right now, find something for them to do. And they’ll knock it out of the park and make you very glad that you did.
Bryan Wish: Intellectual horsepower. So well said. I love that. I’m going to steal that. Sam, is there any other comments that you want to say about what you built at Venga? If I’m pronouncing it right, Venga?
Sam Pollaro: Yeah.
Bryan Wish: Anything else you want to share before I move the conversation along?
Sam Pollaro: No, I think that’s the crux of the story is just it takes a lot of perseverance and sticking with it. And you have to. I always say it’s like rebounding in basketball. I see the basketball Jersey hanging behind you. You never know which way the ball’s going to bounce off the rim. And so you’re not going to get every rebound, but if you hustle enough and you put yourself in a position, eventually the ball is going to bounce your way. And so you have to keep fighting. Even if 4 times, 5 times, 10 times the ball bounces a different way if you keep hustling the ball’s going to bounce you and you’re going to start getting a lot of rebounds.
Bryan Wish: Yeah, absolutely. My mom always, she had a picture of the, I think Michael Jordan quoter, miss 100% of the shots you don’t take. Hoop in my room. But I agree with you. You just got to be hustle, be scrappy and the ball will eventually come your way. Resonate deeply. Sam, question for you. I’m curious about how you grew up. What was your family environment like? Were you always wired this way? I mean, did you have nurturing experiences that maybe drove you to be entrepreneurial? I mean, take us back to maybe Sam the kid before he went off to college or post.
Sam Pollaro: Yeah. Well, I was very fortunate in that my father is also an entrepreneur, and so I had that role model. And now I think it was planted deep within me, although it never occurred to me. I wanted to be a mechanical engineer. And I wanted to go build planes for Boeing. But I saw him, as an entrepreneur, working and I saw that he could do it. And he was had no experience as an entrepreneur. And he just through sheer tenacity and work ethic, made it work. And so I think ultimately I have to credit him for my success as an entrepreneur.
Bryan Wish: Love that. What about your dad? What qualities did he possess that as you look back and growing up that he just had, or his instincts or characteristics about him that you’ve embodied yourself?
Sam Pollaro: Yeah. I mean, the number one is his, the way he balanced his work and career as an entrepreneur with the time as with the family. We would always have dinner together as a family, every single night, right at 6:30. And if he wasn’t home at 6:31, we, my mom and I, would scowl at him when he came in the door. And most of the days, he was absolutely home at 6:30 for our family dinner. And throughout all of it, he was, he always coached my baseball teams. And I think in 12 years of coaching my baseball teams, he may have missed one or two games because he was out of town. But he never missed a game because of some work commitment. So he was able to balance all the work that he had to do as an entrepreneur with the time that he spent with me and my mom and the family.
Bryan Wish: Wow. So special to look back on and have those memories. My dad similar, in a very similar capacity. And it’s something I’m very fond of. So it means a lot. And you have a family, but your parents work very hard. So neat that you have that and can look back on that and see he was always there for you. So very cool. Sam, I want to touch on a bit what you’re doing now. We are talking about this experience, building Venga, these memories is really directly applying to what you’re doing today. And leaning on that for more perseverance, overcome obstacles. Maybe tell us about the company that you’re building right now and your vision for it.
Sam Pollaro: Sure. So I started a company called PicassoMD with… I have two co-founders. One is a doctor who I met, who had the original idea for PicassoMD, as well as my CTO from Venga who now worked together for seven years. We’ve got a great working relationship. And when I started another company, I knew I wanted him to be a part of it. And so what we do is we help primary care doctors get connected with specialists when they have a question about how to treat or triage a patient. So if you walked into your doctor’s office and said “I’m having this chest pains. What should I do?” Your primary care doctor can’t really be expected to know everything about the dozens of medical specialties. But what we do is through our apps essentially give your primary care doctor the ability to be instantly connected with a specialist to help him/her figure out what to do with you, and whether you should go to the emergency room, whether you should go see a specialist for more testing or whether this is nothing to worry about, and just something to continue to monitor.
Bryan Wish: Looks so cool. You’re creating a clear medical path. And I think that’s why I create why I connected with you so much on, I think, our first call a few months ago is because of just my injuries and health battles. And having to jump through 14 different hoops to find the right plan for me. And that journey is mentally taxing, physically taxing. So if you can reduce that. You mentioned to me something on that call from my notes about it really being a benefit to insurance companies, right, and cost savings. Can you maybe speak to that?
Sam Pollaro: Sure. So we spend about $50 billion each year in the US on unnecessary healthcare. And that breaks down into a lot of specialist care. One out of every two specialist visits is unnecessary. And about two out of every three emergency visits are actually for non-emergencies. And so if we can eliminate that unnecessary healthcare and we can better triage patients and get them to the right next levels of care, that reduces the overall costs on our healthcare system, which makes it cheaper for us to buy health insurance, cheaper for us to get healthcare.
But also it makes it easier to see a specialist. If you’re trying to see, get in to see an orthopedist, who specializes in knee injuries, it could take you months to get an appointment. And the problem is that if half of those people, who that orthopedic sees, don’t need to be there could be treated in another environment, right, we can cut those lead times in half or more. So by making sure that the right levels of care are established we reduce unnecessary costs for everyone to make it easier for everyone to access specialty care when they really need it.
Bryan Wish: So, yeah, I love that. I just think at a level of scale, and you can get that to be impacting millions of people every week, every month, right. Tons of million. You can really change lives and health journeys for people. Sam, one more question, and then I want to give people a place to connect. Why Picasso, the name?
Sam Pollaro: So the name was chosen by my co-founder, but it relates to the fact that medicine is as much art as it is science. And there’s so much gray area in treating patients. And it’s not just something that you can look up every answer in a book. And so by bringing specialists into the primary care setting, we help facilitate that art of medicine.
Bryan Wish: Got it. Love the answer. And actually I have one more question. This is a bit morbid, but you just got to stick with me here. If you had cancer, you could only pick one way to heal yourself not knowing how it was going to turn out. And you had an Eastern medicine philosophy, or a Western medicine philosophy which one would you pick? If you had to pick one to heal yourself.
Sam Pollaro: Yeah, that’s really difficult because I’ve seen the successes and failures of both of those. I’ve seen times when our Western medicine was so interventionist that the treatments were worse than the disease, right. And you’d say you should, we do too much. We’re too interventionist. Eastern medicine has its advantage. And then I’ve seen the beauty of close family members who’ve had cancer and have used modern Western medicine treatments, and they’ve been cured and cancer free. So I don’t know. I have to think long about and hard about that. It’s a great question. I think I’d have to evaluate is the treatment protocol that’s being recommended worse than the disease? Or can this be treated a little bit less aggressively, at least first, until it requires a more aggressive intervention?
Bryan Wish: Got it. No, love the answer. I think that’s the hardest question I’ve ever asked someone. So thanks for giving it an attempt. I just wanted to see how you thought about it. Sam, this has been so great. Such polished answers. Not that you tried to be in any way, but just spoke with such clarity. And I appreciate how you went about it and such perseverance along your journey. If people wanted to reach out or be inspired by you, had a question to follow up, what’s the best place to find you?
Sam Pollaro: Yep. Twitter is great. @Sampollaro. S-A-M, P as in Paul, O-L-L-A-R-O.
Bryan Wish: Awesome. Well, Sam, thanks so much. Can’t wait to share this. Best of luck to you on your journey, and super excited for what’s ahead.
Sam Pollaro: Thanks, Bryan. It’s been fun.