FF 006: Acquired by Amazon, CEO @ Digg, EIR @ a16z and now Founder @ Pro.com with Matt Williams

Matt Williams is Founder and CEO of Pro.com. Prior to Pro.com, Matt served as entrepreneur-in-residence at Andreessen Horowitz, following his time at Digg where he led the complete overhaul of Digg which he joined as CEO in 2010 to rebuild the site from the ground up and contributed to its successful acquisition by Betaworks in 2012. Before Digg, Matt spent 12 years at Amazon where he managed Amazon’s Auctions and Marketplace, Community and Cross Merchandising, Tech Alliances, Web Store, and Consumer Payments divisions. Prior to Amazon, Matt founded and was the CEO of Livebid, which was acquired by Amazon in 1999. In Today's Episode You Will Learn: 1.) How Matt made his way into entrepreneurship and then later the VC world? 2.) How did LiveBid come about when Matt was only 23 and how did he build the product and the initial user base? 3.) What was the hardest aspect of the entire LiveBid journey and how did Matt overcome it? 4.) How did Matt's life and work change moving from your own startup to working in a massive organization like amazon? What would Matt advise founders who have sold or are thinking of selling their companies to large corporations? 5.) Following a number of years at Amazon. How did you attempt to turn Digg around as CEO and was their anything you would have done differently? 6.) As EIR at Andreessen Horowitz what was it like, for Matt, working at a16z? Was there anything that surprised Matt about the move to venture? 7.) What would Matt say was the biggest lesson from working at these tech titans was? How has that affected how Matt runs Pro.com today?

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  It's that time of the week, it's Founders Friday and today I could not be more delighted than to welcome a true titan to the tech industry. Having founded LiveBit at 24, he was then acquired by no less than the great Amazon, where he then spent 12 years managing a multitude of divisions before being appointed CEO at my very own favourite, Dig. He then progressed to being Entrepreneur in Residence at the VC giant Anderson Horowitz and now he has reverted back to his founder roots. Since he co-founded Pro.com back in 2013, it's A16Z Jeff Bezos backed and it's an incredible

• 0:41Harry Stebbings?

  interview where we discover the inner workings of the true titans of the tech industry. Our guest today is of course, the legendary Matt Williams. But before we jump into today's interview, I would love to hear what you think of my new show in collaboration with Syndicate Room. It's called Angel Insights and it delves inside the world of angel investing to discover their tactics, tips, tricks and all the metrics that angels really look at when they're analysing seed investments. I would love to hear your thoughts and you can let me know by emailing harry@thetwenty minute vc.com. Likewise, I would love to hear what you think of Founders Friday. Obviously it's a new addition to the show and we would love your feedback and any thoughts you might have on it.

• 1:25Harry Stebbings?

  But ladies and gentlemen, without further ado, it's time to welcome the genius that is Matt Williams, CEO and co-founder at Pro.com.

• 1:43Harry Stebbings?

  Matt, thank you so much for coming on the 20 Minute VC and 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?

• 1:57Speaker 01

  Sure, happy to do so. Today, I am founder and CEO of Pro.com, a marketplace for connecting up homeowners with pros to get anything done in and around the home. And we've been out for about a year, out in the kind of public offering in terms of our our website and offering. We've been in business for just about two years. We were kind of stealth mode for the first year. Before that, I was entrepreneur resident at Andreessen Horowitz, and before that, CEO of Dig.com, and was at Amazon for about 12 years. Prior to that, as GM of a number of different businesses in Amazon, including Community,

• 2:40Speaker 01

  the web store kind of platform, and GM of consumer payments before leaving. And prior to that, I started a company called LiveBit that was founded back in 96 and sold to Amazon in 99 for about a 10x return to investors, and that's how I came into Amazon.

• 3:02Harry Stebbings?

  So you founded LiveBit in 96 when you were 24, I believe.

• 3:06Speaker 01

  Yeah, 23 actually, but yes.

• 3:09Harry Stebbings?

  23, almost, almost.

• 3:10Speaker 01

  That's almost.

• 3:11Harry Stebbings?

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

• 3:17Speaker 01

  Well, it's a great question. It was a very circuitous route, as I think many startups are. We started the company actually as a web technology shop, just kind of building many different products for different people in the industry. And we did some work in the radio industry. We did some work with some banks in terms of transaction handling. We built one of the earliest survey products, so what today might be SurveyMonkey. We built one of the earliest Java search engines. So we actually had built quite a few different products and business lines, and one of them was working with auctioneers.

• 3:59Speaker 01

  We realized that it was kind of the right time and right place with eBay and at the time OnSale and a number of others that were getting hot. And we decided to focus, you know, the entire company on the auction space and build the first real-time, you know, first real-time engine for, for competing in a physical auction for online bidding. And 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. We had, we had hard-to-find items that, that were in, you know, high demand through physical auctioneers getting connected to our platform.

• 4:42Speaker 01

  So, we, we took a very, a very, kind of, a very circuitous route to get to the point of having a product and an, and an offering for the auction industry and partnered with somebody, built the product under the LiveBid name. And in about a year, we're able to amass close to a hundred million dollars in inventory that was, you know, being offered through auction through our website, which at the time was quite a bit. And we then had, had interest from eBay, Yahoo, and Amazon for acquisition.

• 5:18Harry Stebbings?

  And how did you actually get your first customers? Often that's the biggest hurdle for most startup founders, getting the first ones. How did you get yours?

• 5:25Speaker 01

  Well, we had, we had partnered with a company that was, was kind of the foremost auction list online. And through combination of partnerships like that, we, we actually had quite a few connections to auctioneers. And so we, you know, had a small direct sales team and started, you know, started going after the most interesting and hard-to, hard-to-find inventory. We had a lot of classic cars. We, in fact, sold the Batmobile online.

• 5:56Harry Stebbings?

  Wow.

• 5:57Speaker 01

  Through our platform, you know, from the, from one of the Bat, Batman movies.

• 6:01Harry Stebbings?

  How much did that get for?

• 6:02Speaker 01

  It was, it was, if I recall, it was around two hundred and thirty or two hundred and forty thousand dollars.

• 6:11Speaker 01

  Which back in ninety ninety eight uh was a uh was was early days for buying such a thing online.

• 6:18Harry Stebbings?

  And listening to your journey at Livebid, it 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?

• 6:30Speaker 01

  Well, so when we uh when we built the uh 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 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.

• 7:13Speaker 01

  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 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

• 7:55Speaker 01

  who were uh who were helping us and ended up, you know, closing an oversubscribe round of about one point three million in in a matter of uh about three months. And we had one of the largest auction events kind of on that's ever been broadcast online, which is the OJ Simpson Estate Sale.

• 8:13Harry Stebbings?

  Wow, yeah.

• 8:14Speaker 01

  So it's a combination of factors, but really just uh believing in the team, believing in the product, believing in myself and and gritting through uh a tough capital raise and uh and ultimately continuing to drive the business forward, getting high-profile auctions.

• 8:31Harry Stebbings?

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

• 8:40Speaker 01

  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 traction, some very clear product market fit for the offering that you have. And it, it doesn't have to be huge, but it has to be, you know, kind of demonstrated 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.

• 9:24Speaker 01

  I think if, you know, if you have a, uh, you kind of a track record of successful startups and, 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, 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, are looking at is at the right time and right place. And it's, you know, something that, um, you know, Marc 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.

• 10:08Speaker 01

  And, and so I think that, you know, if you, uh, if you have found that kind of market opportunity, uh, then it's a matter of, you know, being able to demonstrate, uh, that you've got the right team and the right beginning of a product if you're going to go raise a, a seed round and, um, being able to, you know, kind of get feedback along the way from VCs, not necessarily in the, in the context of a raise, but in the context of here's what, you know, I'm thinking about doing and I've already gotten some, you know, feedback and traction and, uh, in a beta, right? Or in kind of customer surveying that I've done or whatever the case may be. So really, it really depends on the... You know, on the entrepreneur and and the stage and what industry they're going into.

• 10:51Harry Stebbings?

  And following this tumultuous fund 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 organisation like Amazon? And what would you advise founders who are potentially thinking of selling their companies to large corporations?

• 11:11Speaker 01

  Right, well, I uh prior to starting Livebid, I was I was actually uh a a business analyst uh turned into a uh kind of a a, you know, tech leader inside of NCR Corporation, which was at the time forty five thousand 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 a trail of of, you know, self taught programming, pick up some tools, learn them myself, you know, built some tools inside the company that ended up getting rolled out, kind of company wide, so I I definitely had an appreciation for

• 11:51Speaker 01

  the dynamics of large companies, but, you know, I 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 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 uh that ultimately I uh I needed to get career experience, so I started with a 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.

• 12:34Speaker 01

  Uh it's just tr- truly the drive that you have, the impact that you wanna make, and frankly, the environment. And so if you're being acquired by a company that is that is, you know, highly in inventive, uh innovative, that wants to that uh that truly wants to take the next step in whether it's a product division or whether it's as a company. Uh and Amazon is is, I think, you know, one of the best, if not the best, examples in the world of such a company, then, you know, you'll you'll you'll fit in great. As an entrepreneur, I think if you're joining a legacy company that that that is not, you know, kind of anything described as entrepreneurial or kind of inventive,

• 13:19Speaker 01

  you might have a hard time. And, you know, I I think that very few people, very few founders ever kind of last longer than two or three years at most startups that get then get acquired. I, you know, I think there's there are very few. I happen to be one of the rare, you know, kind of rare ones that I was at Amazon for about 12 years after being acquired.

• 13:40Harry Stebbings?

  And you clearly did fit in great there. And then and then you made the move from Amazon, obviously, to being appointed CEO at Dig.

• 13:48Speaker 01

  Yes.

• 13:49Harry Stebbings?

  A company that was struggling at the time. How did you how did you attempt to kind of turn this around? And was there anything you would have done differently?

• 13:57Speaker 01

  Sure. It's, you know, the experience at Dig was was really a 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, especially in its space. It was, in fact, one of the top, I think, three traffic news websites at one time in its history with 40-plus million monthly unique visitors. And and it had stagnated when I 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.

• 14:38Speaker 01

  Because it was, you know, it was a situation where I'd come in and the community was already in turmoil over the most recent release that that was made by the team before I joined. And it's really required the immediate look at the financials, the headcount, the, you know, the community. And and and so I spent a lot of time trying to trying to understand what the community needed, what the team that we needed to be able to to build that and to run that. And so it was a it was a really hard, you know, kind of first six weeks,

• 15:18Speaker 01

  which included laying off about 40% of the staff. And and so I I think it's, you know, if you if you look back on something like that. It's hindsight is always twenty twenty, but I I don't think anyone coming in. Um could have made a a much different decision other than, you know, kind of get get the burn in line. And uh and really just understand your customer, talk to the community.

• 15:44Harry Stebbings?

  And was there anything you would have done differently there?

• 15:47Speaker 01

  Hmm. Well, I think that's a. That probably would have uh more quickly uh brought in. Some additional talent. Uh that's 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 a stronger. 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 uh that would have been, you know, most immediate uh upon joining.

• 16:31Harry Stebbings?

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

• 16:36Speaker 01

  Well, we uh decided to uh to sell uh sell the company. And 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 we're able to um to get some uh money back for investors. And uh and the team, you know, positioned in a great place. We've lost very few people on the team during that process. Uh which I was very thankful and and proud of and. And uh then I ended up uh having a couple of opportunities to be entrepreneur in residence. And joined uh joined Andreessen. Um Andreessen it had uh had been.

• 17:17Speaker 01

  A early investor in DIG 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 DIG.

• 17:31Harry Stebbings?

  And how is a entrepreneur in residence different to your standard investment analyst at a VC firm? What do you guys do differently?

• 17:39Speaker 01

  I think it's different for every VC and I think it's it is what what you make of it. I think in some VCs it is a it's it's a desk, you know, for you to just have and figure out what you want to do next. And I think for on the other kind of end of the spectrum, you really directly engage and help the portfolio companies. You evaluate new investments, you you know, you take on some projects and and then figure out what you want to do next. And that is exactly what you know what I did spending my time at Andreessen. I got a chance to work with a number of the portfolio companies, especially on the consumer side.

• 18:21Speaker 01

  I got a chance to to to run a couple of projects of my own that I was interested in. There were some data related projects and and then helped evaluate some of the investments. And that were being made at the time and then ultimately figured out that I wanted to build and launch this marketplace for Pro.com.

• 18:45Harry Stebbings?

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

• 19:01Speaker 01

  Well, I think it's the probably the single biggest takeaway is just simply the people that I that I worked with. I have been very lucky in life to work with some of the most remarkable individuals and and kind of leaders. And so I had the chance and opportunity to work very closely with Jeff at Amazon, including shadowing him for a period of time. I got a chance to work, you know, very closely with kind of Ben and Mark when I was, you know, both at Dig and then 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

• 19:44Speaker 01

  There's a very high bar for bringing in 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 individuals who, who, you know, very strong willed. And have, you know, clear opinions about different industries and different businesses and different business models. 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 getting to work closely with Mark, Ben and the rest of the team at Andreessen.

• 20:29Harry Stebbings?

  And if it's okay with you, we're gonna move into a quickfire round now.

• 20:33Speaker 01

  Yep.

• 20:34Harry Stebbings?

  So, favorite book and why?

• 20:37Speaker 01

  Favorite book, I would say is good to great. Because it really takes a data-driven analysis of what makes a company great.

• 20:44Harry Stebbings?

  And then, highlights of your career?

• 20:47Speaker 01

  Highlight of my career was selling, uh, selling my company, uh, at the age of twenty seven. And, uh, being a part of a much larger business and, uh, and picture at Amazon.

• 21:00Harry Stebbings?

  What advice would you give to a ten-year-younger self?

• 21:05Speaker 01

  I would say, uh, never lose determination, uh, when you're starting a company and always, uh. Always continue to have that drive that is the, the rare bit that entrepreneurs have.

• 21:20Harry Stebbings?

  Your favorite blog or kind of reading website?

• 21:24Speaker 01

  I would say it's, uh, Ben Horowitz's blog.

• 21:26Harry Stebbings?

  Okay. And then finally, the next five years for you and pro.com, what's in store?

• 21:33Speaker 01

  Well, the, the vision is to build, uh, to build the, the best place for, uh, customers to. Uh, to find, kind of book and pay for any local services and we're starting in and around the home. And that is the, the industry focus that we have today. Uh, but the vision truly is to make. The kind of lack of transparency, the, uh, the lack of immediacy of access, the, uh, you know, the, the simplicity of being able to book and pay for a local service, much easier than it is today. So that's what's in store for pro.com is to bring that to a reality.

• 22:13Harry Stebbings?

  Well, Matt, thank you so much for coming on the show. It's been fantastic having you.

• 22:17Speaker 01

  Thanks, Harry. Appreciate it.

• 22:18Harry Stebbings?

  What an amazing interview, delving into the career of a true legend of the technology industry. And as always, all the items and resources mentioned in today's show can be found on the blog at www dot the twenty minute vc dot com. And as I said earlier, I would love to hear what you think of the new show, Angel Insights, and, and you can email me your thoughts on that at harry at the twenty minute vc dot com, or you can tweet us at Syndicate Room. As I said, I'd love any feedback you might have. Thank you so much, and we can't wait to see you in the next episode.