Jul 31, 2015 · 22m · news
FF 006: Acquired by Amazon, CEO @ Digg, EIR @ a16z and now Founder @ Pro.com with Matt Williams
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of Founders Friday, host Harry Stebbings interviews veteran tech entrepreneur Matt Williams about his career journey from founding LiveBid and selling it to Amazon, to navigating crisis management as CEO of Digg, serving as an EIR at Andreessen Horowitz, and launching Pro.com.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 19.6% of the talking time here. How this is scored →
Harry as informed peer 1.7 Guest teaching 3.1 Guest disagreement 0.3 Harry pushing back 1.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 3:07 Polite age correction
In a very friendly interview, Matt's mildest pushback is correcting Harry's age statement from 24 to 23 years old when founding LiveBid.
Hardest push from Harry ▶ 15:44 Follow-up on Digg turnaround mistakesHarry presses Matt by repeating his sub-question about what Matt would have done differently at Digg after Matt initial response omitted it.
Biggest teaching moment ▶ 8:40 Framework for startup fundraising and market timingMatt delivers authoritative expertise breaking down founder funding strategies by stage and explaining Marc Andreessen's views on market timing.
Harry holds his own ▶ 13:47 Contextualizing Digg's struggling stateHarry exhibits informed context by noting that Digg was struggling at the time Matt was appointed CEO, directing the frame towards turnaround execution.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Matt Williams' Background and Entrepreneurial Origins | 2 | 2 | 1 | 1 | Harry opens with an enthusiastic background overview but gets slightly corrected on Matt's age at LiveBid's founding. Matt then explains LiveBid's early history and technical pivots. | |
| LiveBid's Customer Acquisition and Selling the Batmobile | 2 | 3 | 0 | 1 | Harry challenges the impression that LiveBid was smooth sailing, prompting Matt to reveal severe startup struggles including board pressure to shut down and charging salaries on credit cards. | |
| Fundraising Strategy and Market Timing Advice | 1 | 4 | 0 | 0 | Matt educates the host on fundraising tactics, contrasting advice for first-time founders against repeat founders and highlighting market opportunity size as the critical VC factor. | |
| Acquisition by Amazon and Corporate Intrapreneurship | 1 | 3 | 0 | 0 | Matt details his family background in entrepreneurship and explains the distinction between being an intrapreneur in a big innovative company versus an entrepreneur. | |
| Managing the Turnaround and Hard Decisions at Digg | 3 | 4 | 1 | 4 | Harry demonstrates background knowledge on Digg's decline and explicitly re-asks what Matt would have done differently when Matt skips over it initially. | |
| Experience as Entrepreneur-in-Residence at Andreessen Horowitz | 2 | 4 | 0 | 1 | Harry asks a precise operational question about how an EIR differs from a standard VC analyst, leading Matt to explain the spectrum of EIR roles. | |
| Key Takeaways from Working with Tech Leaders | 1 | 2 | 0 | 0 | Matt shares takeaways from working directly with Jeff Bezos and Andreessen Horowitz founders before completing a quick-fire question round. |
Statements from this episode (12)
Matt Williams: LiveBid delivered a 10x return when acquired by Amazon
“I started a company called LiveBid that was founded back in 96 and sold to Amazon in 99 for about a 10 X return to investors”
LiveBid built the first real-time engine for physical online auctions
“And we decided to focus you know, the entire company on the auction space and built the first real time the real, you know, first real time engine for competing in a physical auction for online bidding.”
LiveBid amassed $100M in inventory before acquisition interest from Amazon and eBay
“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 acq…”
Matt Williams: LiveBid sold an official movie Batmobile online in 1998
“We in fact sold the Batmobile online. Wow. Through our platform, you know, from the from one of the Batman movies.”
Matt Williams funded LiveBid employee salaries with his personal credit card
“You know, I was already at the point of starting to put, you know, salaries on my credit card for those employees that had families.”
LiveBid broadcast the OJ Simpson estate sale as an online auction
“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.”
Matt Williams: First-time founders should bootstrap until achieving clear product-market fit
“So if it is a if it's a relatively new founding team that's never founded another company 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 h…”
Matt Williams: Most acquired founders leave within three years; he stayed twelve
“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 yea…”
Matt Williams: Digg reached over 40 million monthly unique visitors at peak
“It was, in fact, one of the top, I think, three traffic news websites at one time in its history with forty-plus million monthly unique visitors”
Matt Williams laid off 40% of Digg staff in his first six weeks
“It was a really hard, you know, kind of first six weeks, which included laying off about 40% of the staff”
Matt Williams: Digg turnaround needed fresh outside talent sooner after v4 launch
“That probably would have more quickly brought in some additional talent that that, that hadn't kind of lived through the pain of, you know, kind of the V four launch and brought in new blood more, kind of more quickly to really help not only carry new perspect…”
Matt Williams: EIR roles range from passive holding desks to active support
“I think it's different for every VC, and I think it's, it is what you make of it. I think in some VCs, it is a 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 re…”