Picasso and Pollaro: Together at Last

It makes sense that Sam Pollaro took my interview while on a walk. After all, he runs a medical technology company. More on that later. First, allow me to introduce young Sam: young Sam was obsessed with planes and cars. He wanted to be an engineer when he grew up.

For a while, he—older Sam, that is—was. It didn’t take, though. “When you’re a kid, you think engineering means you’re gonna be designing planes or cars. But in reality, what you’re doing is designing the bracket that holds the rear-view mirror in place on the car. And that’s just a lot less fun…” Instead, Sam went into finance. Which was great until 2009. He got back from a sabbatical to find that the investment company he worked for was putting up the shutters. “It was the height of the financial crisis,” he told me. “And so, it wasn’t easy to find a new job in finance, so I decided this would be the opportunity to start a company.” He describes it as something of a Blue Apron for flower subscriptions. “Every week, customers would get a bundle of flowers, and we would show them how to arrange it…” After two years, Sam and his team sold this company to another flower subscription operator, and Sam moved on.

His next venture was collaborating with a former colleague on a new business called Venga, which Sam described as an “anti-Groupon…We wanted to build a platform that would enable restaurants to reach new consumers with all the cool things that they were doing in a digital environment. So, if they were having happy hours or wine tastings, or kids-eat-free nights, there was really no way for them to reach the public other than their social media…”

They started with a consumer app and some creative advertising. “We were doing all these guerrilla tactics—like we bought an old-school bus and had it wrapped in our colors and logo, and we were driving around town…” The result? “The restaurants loved it—or they loved the concept of it. But we had a hard time getting consumers to change behavior…” Changing consumer behavior, Sam told me, is expensive: “a lot of these companies

were spending fifty dollars just to acquire one new user…” That wasn’t something Venga could match. Plus, Groupon had quite a hold on the public.

A Plan B materialized: Venga was going to “help restaurants build out a more modern loyalty program. So rather than hand out a punch card, and you get ten punches and you get a free sandwich, we were helping them digitize that.” As time went on, they learned. “The breakthrough was figuring out that we could integrate the point-of-sale system at the restaurant with the reservation system, like OpenTable, and combine the two data sets to keep track of how often people came, how much they spent, and what they liked to eat and drink without anyone having to do anything. This is all happening in the background. So, the consumer didn’t have to sign up, didn’t have to identify themselves, or give their phone number each time they came. All they had to do was make a reservation, and we would automatically track them. This was the big breakthrough that enabled us to really grow the business.”

This yielded a successful exit for Sam and his partners: “we ran it for eight or nine years, and then we sold it to the parent company of OpenTable…”

THE ART OF MEDICINE

PicassoMD was an idea a cardiologist brought to Sam in late 2019. It enables doctors to get clinical feedback from specialists immediately (while the patient is in office) in order to cut down on the number of doctors’ visits patients need to get a diagnosis and start treatment. “So, if you go to your doctor, and you have a rash on your arm, they can say, ‘Go see a dermatologist…with PicassoMD, they can connect to a dermatologist in under thirty seconds and get them to give their feedback on the patient’s condition while the patient’s still in the primary care provider’s office.”

Obviously, PicassoMD deviates a bit from Sam’s previous entrepreneurial resume. What drew him to the medical field? “For one, I was fortunate enough to have a couple successful exits, and so I wanted to do something that was a little bit more mission focused…I also wanted to do something that was at a bigger scale than I had done before.”

Sam had pointed out to me that Venga was a business serving two fronts: consumers and restaurants. Healthcare? That’s a three-front operation, he noted later in our conversation. Patients, doctors, and insurance companies. “It might be a very different pitch depending on which part of the value chain you know you’re going after.”

SAM ON SALES

This here is a Maestro blog, so I hope you didn’t think we’d leave without some sales advice. When I asked Sam what qualities he looks for in a sales professional, he said they needed to know how to listen—“really deeply listen…probably, we spend too much time emphasizing how good a salesperson is at pitching. But you know, lots of people can pitch a product. But what’s really a differentiator is how well they can ask questions to understand the pain points and really listen to what’s not being said as much as what’s being said…” Also: “Being process oriented. I think a lot of salespeople focus on building relationships, being liked, and not really asking hard questions about, ‘Well, what’s your budget?’ ‘What’s your timeline? Who are the decision-makers? ‘What happens if you don’t make this purchase?’ Really understanding the buying process from their prospects’ perspective.”

I was practically contractually obligated to throw in that this idea aligned with a lot of Maestro teachings. To which Sam responded, “That’s where I learned it from…”

You can learn more about Sam here. Be sure to congratulate him while you’re there!