The Exchanges

Q Matt, thank you so much for coming on the 20 Minute VC in this special episode of Founders Friday. Now, can you start us off with a little background on yourself and your entrepreneurial origins and how you really made your journey?

A Sure, happy to do so. Today, I am a founder and a CEO of Pro.com, a marketplace for connecting up homeowners with Pros to get anything done in and around the home. And we've, uh, we've been out for about a year under, uh, uh, out in the, you know, kind of public offering in terms of our, our, uh, website and offering. We've been in business for just about, uh, two years. Uh, we were kind of stealth mode for the first year. Before that, I, uh, was entrepreneur in residence at Andreessen Horwitz. And before that, CEO of dig.com and, uh, was at Amazon for about 12 years. Uh, prior to that as a GM of a number of different businesses in Amazon, including Community. Uh, the web store kind of platform and, uh, and, uh, GM of, uh, consumer payments, uh, before leaving. And, uh, prior to that, I started a company called LiveBid that, uh, was founded back in 96 and sold to Amazon in 99, uh, for about a 10 X return to investors, and, and that's how I, uh, came into, uh, came into Amazon.

AI assessment note: “I started a company called LiveBid that, uh, was founded back in 96”

Q And listening to your journey at LiveBid, it all, it all sounds like, you know, it was all smooth sailing, but I'm sure it wasn't, so what was the hardest aspect for you of the LiveBid journey, and how did you overcome it?

A Well, so when we, uh, when we built the, um, the, the company, it was heavily fueled off of our revenues, and so we had, uh, we had originally built the company off of, uh, you know, doing, you know, kind of building web technology for, you know, for the enterprise and for, you know, many different, you know, products for businesses, so we were heavily self-funded. We raised a very small amount of seed capital, and, uh, I had a, a, a advisory board that was helping me, Kind of construct a, uh, a capital raise and, uh, bring in some additional management team, and it was, uh, it was particularly hard because I had direct feedback from my advisory board to shut down, and that, uh, we just weren't, you know, we weren't going to, uh, be able to raise the capital. We needed to bring in a CEO, uh, because I was, you know, very young, and that, uh, You know, I was, I was already at the point of starting to put, you know, salaries on my credit card for, for, uh, those employees that had families. So it was a, uh, very tumultuous time. And, uh, and that's really when we started seeing kind of product market fit and traction for these auction events. And we, uh, I, I then personally went and, um, and, you know, did all of the capital raising myself instead of relying on some others who, uh, Who were, uh, who were helping us and ended up, you know, closing an oversubscribed round of about…

AI assessment note: “it was particularly hard because I had direct feedback from my advisory board to shut down”

Q And having endured a tough capital raise, what would you advise founders potentially entering, entering into a round of funding?

A Well, it really depends on the, on the timing of where they are as a company and really the, the history of the, the founding team. So if, if it is a, uh, if it's a relatively new founding team that's never founded another company, uh, my advice is quite simple, which is to bootstrap as long as you can until you see some very clear, uh, traction, some very clear product market fit For the offering that you have, and it doesn't have to be huge, but it has to be, you know, kind of demonstrated, uh, product market fit, that you're in the right space at the right time, and that there's, you know, significant demand for what you're offering. I think if, you know, if you have a, uh, kind of a track record of successful startups and, you And you are, uh, you know, you are trying to raise kind of seed capital or growth capital. I think it's, you know, you, uh, you want to prove out kind of the, the model that the, the market opportunity is huge. I think that still is the primary kind of factor that most, you know, most VCs are looking at is at the right time and right place. And it's, you know, something that, um, you know, Mark Andreessen has said many times in terms of what can kill a startup is, is, uh, you know, being in the wrong place at the wrong time in terms of the, you know, not having a market opportunity that is a groundswell. And, and so I think that, you know, if you, uh,…

AI assessment note: “my advice is quite simple, which is to bootstrap as long as you can”

Q How did the company come about, uh, and how did you build the initial product and user base?

A Well, it's a, it's a, it's a great question. It was a very circuitous route, as I think many, many startups, uh, many startups are. We, uh, we started the company actually as a, as a web technology shop, just kind of building many different products for different people in the industry. Um, and, uh, and we did some work in the radio, uh, radio industry. We did some work, uh, with some banks in terms of transaction handling. We built one of the earliest survey products, so, uh, what today might be SurveyMonkey. Um, we built one of the earliest Java search engines, so we, we actually had, had built quite a few different products and business lines, and one of them was working with auctioneers. We, uh, We realized that it was kind of the right time and right place with eBay and at the time on sale and a number of others that were getting hot. And we decided to focus, uh, you know, the entire company on the auction space and built the first real time, uh, the real, you know, first real time engine for, for competing in a physical auction for online bidding. And, uh, so you can imagine whether it be a Sotheby's Christie's or a, you know, a local regional auctioneer, That has an entire collection of Coca-Cola memorabilia or a classic car auction. Uh, we had, um, you know, we had, uh, hard to find items that, uh, that were in, you know, high demand, uh, through physical auctioneers ge…

AI assessment note: “We started the company actually as a, as a web technology shop”

Q How did the company come about, uh, and how did you build the initial product and user base?

A Well, it's a, it's a, it's a great question. It was a very circuitous route, as I think many, many startups, uh, many startups are. We, uh, we started the company actually as a, as a web technology shop, just kind of building many different products for different people in the industry. Um, and, uh, and we did some work in the radio, uh, radio industry. We did some work, uh, with some banks in terms of transaction handling. We built one of the earliest survey products, so, uh, what today might be SurveyMonkey. Um, we built one of the earliest Java search engines, so we, we actually had, had built quite a few different products and business lines, and one of them was working with auctioneers. We, uh, We realized that it was kind of the right time and right place with eBay and at the time on sale and a number of others that were getting hot. And we decided to focus, uh, you know, the entire company on the auction space and built the first real time, uh, the real, you know, first real time engine for, for competing in a physical auction for online bidding. And, uh, so you can imagine whether it be a Sotheby's Christie's or a, you know, a local regional auctioneer, That has an entire collection of Coca-Cola memorabilia or a classic car auction. Uh, we had, um, you know, we had, uh, hard to find items that, uh, that were in, you know, high demand, uh, through physical auctioneers ge…

AI assessment note: “We started the company actually as a, as a web technology shop”

Q And then how did you make your transition to Anderson Horowitz? How did that come about?

A Well, we, uh, decided to, uh, to sell, uh, sell the company and, uh, sell Dig, and, uh, ended up, uh, running a process and really working that process, you know, very, very thoroughly, and we, uh, you know, we ultimately completed that, uh, were able to, um, to get some money back for investors, and, uh, and the team, you know, positioned in a great place. We lost very few people on the team during that process, uh, Uh, which I was very thankful and proud of and, and, uh, and then, uh, ended up, uh, having a couple of opportunities to be entrepreneur in residence and joined, uh, joined Andreessen. Andreessen had, uh, had been a, uh, early investor in Digg and, and, uh, uh, participants on the, on the board and, and were very helpful, both Ben and Mark in, uh, the kind of ups and downs and the trials and tribulations of, of Digg.

AI assessment note: “having a couple of opportunities to be entrepreneur in residence and joined, uh, joined Andreessen.”

Q And having endured a tough capital raise, what would you advise founders potentially entering, entering into a round of funding?

A Well, it really depends on the, on the timing of where they are as a company and really the, the history of the, the founding team. So if, if it is a, uh, if it's a relatively new founding team that's never founded another company, uh, my advice is quite simple, which is to bootstrap as long as you can until you see some very clear, uh, traction, some very clear product market fit For the offering that you have, and it doesn't have to be huge, but it has to be, you know, kind of demonstrated, uh, product market fit, that you're in the right space at the right time, and that there's, you know, significant demand for what you're offering. I think if, you know, if you have a, uh, kind of a track record of successful startups and, you And you are, uh, you know, you are trying to raise kind of seed capital or growth capital. I think it's, you know, you, uh, you want to prove out kind of the, the model that the, the market opportunity is huge. I think that still is the primary kind of factor that most, you know, most VCs are looking at is at the right time and right place. And it's, you know, something that, um, you know, Mark Andreessen has said many times in terms of what can kill a startup is, is, uh, you know, being in the wrong place at the wrong time in terms of the, you know, not having a market opportunity that is a groundswell. And, and so I think that, you know, if you, uh,…

AI assessment note: “my advice is quite simple, which is to bootstrap as long as you can”

Q And was there anything you would have done differently there?

A Hmm. Well, I think that, uh, That probably would have, um, more quickly, uh, brought in some additional talent, uh, that, uh, that, that hadn't kind of lived through the, uh, the pain, uh, of, uh, of, you know, kind of the, uh, the V four launch and brought in new blood more, kind of more quickly to, to really help not only carry new perspective, but also, you know, carry, um, you know, a, uh, a stronger, uh, Kind of will and drive to, uh, you know, to, to make it happen. So that's, uh, that's probably the, you know, the only thing that I could think of that, that would have been, you know, most immediate, uh, upon joining.

AI assessment note: “more quickly, uh, brought in some additional talent”

Q And listening to your journey at LiveBid, it all, it all sounds like, you know, it was all smooth sailing, but I'm sure it wasn't, so what was the hardest aspect for you of the LiveBid journey, and how did you overcome it?

A Well, so when we, uh, when we built the, um, the, the company, it was heavily fueled off of our revenues, and so we had, uh, we had originally built the company off of, uh, you know, doing, you know, kind of building web technology for, you know, for the enterprise and for, you know, many different, you know, products for businesses, so we were heavily self-funded. We raised a very small amount of seed capital, and, uh, I had a, a, a advisory board that was helping me, Kind of construct a, uh, a capital raise and, uh, bring in some additional management team, and it was, uh, it was particularly hard because I had direct feedback from my advisory board to shut down, and that, uh, we just weren't, you know, we weren't going to, uh, be able to raise the capital. We needed to bring in a CEO, uh, because I was, you know, very young, and that, uh, You know, I was, I was already at the point of starting to put, you know, salaries on my credit card for, for, uh, those employees that had families. So it was a, uh, very tumultuous time. And, uh, and that's really when we started seeing kind of product market fit and traction for these auction events. And we, uh, I, I then personally went and, um, and, you know, did all of the capital raising myself instead of relying on some others who, uh, Who were, uh, who were helping us and ended up, you know, closing an oversubscribed round of about…

AI assessment note: “direct feedback from my advisory board to shut down”

Q And then how did you make your transition to Anderson Horowitz? How did that come about?

A Well, we, uh, decided to, uh, to sell, uh, sell the company and, uh, sell Dig, and, uh, ended up, uh, running a process and really working that process, you know, very, very thoroughly, and we, uh, you know, we ultimately completed that, uh, were able to, um, to get some money back for investors, and, uh, and the team, you know, positioned in a great place. We lost very few people on the team during that process, uh, Uh, which I was very thankful and proud of and, and, uh, and then, uh, ended up, uh, having a couple of opportunities to be entrepreneur in residence and joined, uh, joined Andreessen. Andreessen had, uh, had been a, uh, early investor in Digg and, and, uh, uh, participants on the, on the board and, and were very helpful, both Ben and Mark in, uh, the kind of ups and downs and the trials and tribulations of, of Digg.

AI assessment note: “having a couple of opportunities to be entrepreneur in residence and joined, uh, joined Andreessen.”

Q And was there anything you would have done differently there?

A Hmm. Well, I think that, uh, That probably would have, um, more quickly, uh, brought in some additional talent, uh, that, uh, that, that hadn't kind of lived through the, uh, the pain, uh, of, uh, of, you know, kind of the, uh, the V four launch and brought in new blood more, kind of more quickly to, to really help not only carry new perspective, but also, you know, carry, um, you know, a, uh, a stronger, uh, Kind of will and drive to, uh, you know, to, to make it happen. So that's, uh, that's probably the, you know, the only thing that I could think of that, that would have been, you know, most immediate, uh, upon joining.

AI assessment note: “brought in some additional talent, uh, that, uh, that, that hadn't kind of lived through”

Q How did you, how did you attempt to kind of turn this round, and was there anything you would have done differently?

A Sure. It's, uh, you know, the experience at, uh, Dig, uh, Uh, was, uh, was really a, uh, kind of fascinating one, a, an amazing kind of history, and frankly, one of the top, you know, kind of high flyers of, of, of traffic, uh, especially in its space. It was, in fact, one of the top, I think, three, um, traffic news websites at one time in its history with forty-plus million monthly unique visitors, and, and it had, It stagnated when I, uh, when I came in and then was in a major kind of turnaround scenario. And I, I'll, you know, be really candid. It was the hardest job of my life, uh, because it was, you know, it was, uh, uh, a situation where I'd come in and the community was already in turmoil over the most recent release that, uh, that was made, uh, by the team, uh, before I joined. And it's, uh, Really required an immediate look at the financials, the head count, the, you know, the community, and, and, uh, and so I spent a lot of time trying to, trying to understand what the community needed, what the, uh, team that we needed to be able to, to build that and to run that, and so it was a, uh, it was a really hard, you know, kind of first six weeks, which included laying off about 40% of the staff, and, um, And so, I, I think it's, you know, if you, if you look back on something like that, it's, uh, hindsight is always twenty-twenty, but I don't think anyone coming in, um, …

AI assessment note: “I don't think anyone coming in, um, could have made a, a much different decision”

Q How did you, how did you attempt to kind of turn this round, and was there anything you would have done differently?

A Sure. It's, uh, you know, the experience at, uh, Dig, uh, Uh, was, uh, was really a, uh, kind of fascinating one, a, an amazing kind of history, and frankly, one of the top, you know, kind of high flyers of, of, of traffic, uh, especially in its space. It was, in fact, one of the top, I think, three, um, traffic news websites at one time in its history with forty-plus million monthly unique visitors, and, and it had, It stagnated when I, uh, when I came in and then was in a major kind of turnaround scenario. And I, I'll, you know, be really candid. It was the hardest job of my life, uh, because it was, you know, it was, uh, uh, a situation where I'd come in and the community was already in turmoil over the most recent release that, uh, that was made, uh, by the team, uh, before I joined. And it's, uh, Really required an immediate look at the financials, the head count, the, you know, the community, and, and, uh, and so I spent a lot of time trying to, trying to understand what the community needed, what the, uh, team that we needed to be able to, to build that and to run that, and so it was a, uh, it was a really hard, you know, kind of first six weeks, which included laying off about 40% of the staff, and, um, And so, I, I think it's, you know, if you, if you look back on something like that, it's, uh, hindsight is always twenty-twenty, but I don't think anyone coming in, um, …

AI assessment note: “I don't think anyone coming in, um, could have made a, a much different decision”

Q And following this tumultuous funding round for you, you were then obviously acquired by Amazon. How did your life and work change moving from your own startup to working in a huge organization like Amazon? And what would you advise founders who are potentially thinking of selling their companies to large corporations?

A Right. Well, I, uh, prior to starting LiveBid, I was, uh, I was actually, uh, a business analyst, uh, turned into a, uh, kind of a, a, you know, tech leader inside of, uh, NCR Corporation, which was, at the time, 45,000 people. So, I had, I had some early career experience in very large companies, and, uh, I'd actually kind of blazed, uh, you know, a trail of, of, You know, self-taught programming, pick up some tools, learn to myself, you know, build some tools inside the company that ended up getting rolled out kind of company-wide. So I, I definitely had an appreciation for the dynamics of large companies, but, you know, I, I come from a family of entrepreneurs. My mother, father, stepfather, they all started different businesses in different industries. My, Father in the radio industry, my mother, one of the largest Montessori schools on the West Coast, and my stepfather owned his own construction company and was a contractor. And so, you know, having learned a lot, I knew that my path was going to be one of entrepreneurial nature, but that, ah, that ultimately, I, ah, I needed to get career experience, so I started with a, ah, fairly large company. The, the, the only advice I guess I would give is that there's There's a lot of similarity, uh, between being an intrapreneur and an entrepreneur. Uh, it's just truly the drive that you have, the impact that you want to make, and…

AI assessment note: “The, the, the only advice I guess I would give is that there's”

Q And looking back at the incredible companies, you know, Dig, Amazon, uh, Anderson Horror, it's truly Titan Tech companies. What did you learn from those experiences, and how's that changed how you run Pro.com today?

A Well, I think it's the, uh, probably the single biggest takeaway is just simply the people that I, that I worked with. I have been, uh, very lucky in life to work with, uh, some of the, you know, most remarkable, uh, individuals and, and kind of leaders, and so I had the chance and opportunity to work very closely with Jeff at Amazon, uh, including shadowing him for a period of time. I got a chance to work, you know, very, uh, closely with, Uh, kind of Ben, uh, and Mark, uh, when I was, you know, both at Digg and then, uh, and then a part of the Andreessen team. And the, you know, frankly, the entire team at Amazon was phenomenal, both from the executive level all the way through and through. Amazon has a, uh, It's a very high bar for bringing in, ah, kind of phenomenal talent. And Andreessen, the same. The team at Andreessen is just, is top notch, and they're truly building a different model, you know, in the industry. And so, you know, the opportunity to work with, uh, individuals who, who, you know, very strong willed and, uh, have, you know, clear opinions, uh, about different industries and different businesses and different business models, uh, Really formed, uh, formed, you know, who I am today, and I'm just very thankful for that opportunity, both on the product side in terms of working directly with Jeff, and then on the, kind of, the company building side in terms of …

AI assessment note: “single biggest takeaway is just simply the people that I, that I worked with.”

Q And looking back at the incredible companies, you know, Dig, Amazon, uh, Anderson Horror, it's truly Titan Tech companies. What did you learn from those experiences, and how's that changed how you run Pro.com today?

A Well, I think it's the, uh, probably the single biggest takeaway is just simply the people that I, that I worked with. I have been, uh, very lucky in life to work with, uh, some of the, you know, most remarkable, uh, individuals and, and kind of leaders, and so I had the chance and opportunity to work very closely with Jeff at Amazon, uh, including shadowing him for a period of time. I got a chance to work, you know, very, uh, closely with, Uh, kind of Ben, uh, and Mark, uh, when I was, you know, both at Digg and then, uh, and then a part of the Andreessen team. And the, you know, frankly, the entire team at Amazon was phenomenal, both from the executive level all the way through and through. Amazon has a, uh, It's a very high bar for bringing in, ah, kind of phenomenal talent. And Andreessen, the same. The team at Andreessen is just, is top notch, and they're truly building a different model, you know, in the industry. And so, you know, the opportunity to work with, uh, individuals who, who, you know, very strong willed and, uh, have, you know, clear opinions, uh, about different industries and different businesses and different business models, uh, Really formed, uh, formed, you know, who I am today, and I'm just very thankful for that opportunity, both on the product side in terms of working directly with Jeff, and then on the, kind of, the company building side in terms of …

AI assessment note: “Really formed, uh, formed, you know, who I am today”

Q And following this tumultuous funding round for you, you were then obviously acquired by Amazon. How did your life and work change moving from your own startup to working in a huge organization like Amazon? And what would you advise founders who are potentially thinking of selling their companies to large corporations?

A Right. Well, I, uh, prior to starting LiveBid, I was, uh, I was actually, uh, a business analyst, uh, turned into a, uh, kind of a, a, you know, tech leader inside of, uh, NCR Corporation, which was, at the time, 45,000 people. So, I had, I had some early career experience in very large companies, and, uh, I'd actually kind of blazed, uh, you know, a trail of, of, You know, self-taught programming, pick up some tools, learn to myself, you know, build some tools inside the company that ended up getting rolled out kind of company-wide. So I, I definitely had an appreciation for the dynamics of large companies, but, you know, I, I come from a family of entrepreneurs. My mother, father, stepfather, they all started different businesses in different industries. My, Father in the radio industry, my mother, one of the largest Montessori schools on the West Coast, and my stepfather owned his own construction company and was a contractor. And so, you know, having learned a lot, I knew that my path was going to be one of entrepreneurial nature, but that, ah, that ultimately, I, ah, I needed to get career experience, so I started with a, ah, fairly large company. The, the, the only advice I guess I would give is that there's There's a lot of similarity, uh, between being an intrapreneur and an entrepreneur. Uh, it's just truly the drive that you have, the impact that you want to make, and…

AI assessment note: “The, the, the only advice I guess I would give is that there's”