In this episode of Founders Friday, the host welcomes Matt Williams, a seasoned entrepreneur and tech industry leader. Williams shares his journey from founding LiveBid at 23, which sold to Amazon, to his 12-year tenure at Amazon leading various divisions, and his CEO role at Digg. He also discusses his time as an entrepreneur in residence at Andreessen Horowitz and his return to founding with Pro.com, a marketplace connecting homeowners with professionals for home services. Williams reflects on the importance of product-market fit, the challenges of fundraising, and advises bootstrapping until clear traction is demonstrated. He emphasizes the value of working with talented individuals and the lessons learned from tech giants like Amazon and Andreessen Horowitz in shaping his approach to running Pro.com. The episode concludes with Williams' aspirations for Pro.com to simplify the process of booking and paying for local services.
"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 Livebid at 24, he was then acquired by no less than the great Amazon, where he then spent twelve years managing a multitude of divisions before being appointed CEO at my very own favorite dig."
The quote introduces the segment and Matt Williams, highlighting his achievements and impact in the tech industry.
"It's a 16 Z Jeff Bezos backed and it's an incredible interview where we discover the inner workings of the true titans of the tech industry."
This quote emphasizes the significance of Pro.com's backing by Jeff Bezos and the venture capital firm 16 Z, setting the stage for an insightful interview about the tech industry.
"I would love to hear what you think of my new show in collaboration with Syndicate Room."
Harry is seeking audience engagement and feedback on his new venture, Angel Insights, showing a commitment to audience interaction and continuous improvement.
"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."
The quote describes Matt's current venture, Pro.com, and its business model.
"Before that I was entrepreneurial residence at Andreessen Horowitz and before that CEO of Dig and was at Amazon for about twelve years prior to that as GM of a number of different businesses in Amazon, including community, the web store kind of platform, and GM of consumer payments before leaving."
This quote provides a summary of Matt's career trajectory, showcasing his experience in various leadership roles across the tech industry.
"And prior to that I started a company called Live Bid that was founded back in 96 and sold to Amazon in 99 for about a ten x return to investors."
Matt's early success with Live Bid is highlighted, indicating his long-standing entrepreneurial spirit and success in the tech sector.
"We started the company actually as a web technology shop, just kind of building many different products for different people in the industry."
This quote explains the origins of Live Bid as a diverse web technology provider before focusing on the auction market.
"We decided to focus the entire company on the auction space and built the first real time engine for competing in a physical auction for online bidding."
Matt describes the strategic pivot to the auction space, which proved to be a successful move for Live Bid.
"In about a year we're able to amass close to $100 million in inventory that was being offered through auction, through our website, which at the time was quite a bit."
The quote showcases Live Bid's rapid growth and success in the auction industry, leading to significant inventory and revenue.
"We then had interest from eBay, Yahoo and Amazon for acquisition."
This quote indicates the competitive interest in acquiring Live Bid, underscoring the company's value and Matt's achievement as a founder.## Initial Acquisition of Inventory
Well, we had partnered with a company that was kind of the foremost auction list online. And through a combination of partnerships like that, we actually had quite a few connections to auctioneers.
This quote explains the strategic partnerships that facilitated the acquisition of their initial inventory and their approach to sourcing unique items for auction.
We had a lot of classic cars. We in fact sold the Batmobile online.
Matt Williams highlights a significant sale that exemplifies the type of unique inventory they dealt with, showcasing the early potential of online auctions.
And it was particularly hard because I had direct feedback from my advisory board to shut down, and that we weren't going to be able to raise the capital we needed to bring in a CEO because I was very young and that I was already at the point of starting to put salaries on my credit card for those employees that had families.
This quote reflects the dire financial situation and the skepticism from the advisory board that Matt Williams faced, illustrating the significant risk and personal investment involved.
And I then personally went and did all of the capital raising myself instead of relying on some others who were helping us, and ended up closing an oversubscribe round of about 1.3 million in a matter of about three months.
Matt Williams shares his proactive approach to overcoming the funding challenge, which led to a successful capital raise that allowed the company to continue operating and growing.
It really depends on the timing of where they are as a company and really the history of the founding team.
The quote suggests that the strategy for raising funds is highly dependent on the stage of the company and the experience of the founding team, indicating that there is no one-size-fits-all approach to funding.
I think that still is the primary kind of factor that most vcs are looking at is at the right time and right place.
Matt Williams points out the critical factor for venture capitalists, which is the startup's positioning in terms of timing and market opportunity.
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If I recall, it was around 230 or $240,000, which back in 98 was early days. For buying such a thing online and.
This quote provides context for the scale and novelty of selling high-value items like the Batmobile online during the late 1990s.
We had one of the largest auction events kind of that's ever been broadcast online, which was the OJ Simpson estate sale.
Matt Williams mentions this event as a milestone, demonstrating the company's capability to handle significant and high-profile auctions.## Early Career and Entrepreneurial Background
"So I definitely had an appreciation for the dynamics of large companies."
This quote highlights Matt's understanding of large corporate structures due to his experience at NCR Corporation.
"My mother, father, stepfather, they all started different businesses in different industries."
Matt's family background is deeply rooted in entrepreneurship, which influenced his career path.
"There's a lot of similarity between being an entrepreneur and an entrepreneur."
Matt discusses the commonalities between entrepreneurs and intrapreneurs, focusing on drive and impact.
"It was a situation where I had come in and the community was already in turmoil over the most recent release that was made by the team before I joined."
Matt describes the tumultuous state of Digg's community upon his arrival as CEO.
"I think if you look back on something like that, hindsight is always 2020, but I don't think anyone coming in could have made a much different decision other than kind of get the burn in line and really just understand your customer, talk to the community."
He reflects on the difficult decisions he had to make and the importance of understanding the customer base.
"Well, I think that probably would have more quickly brought in some additional talent that hadn't kind of lived through the pain of kind of the v four launch and brought in new blood more kind of more quickly."
In retrospect, Matt believes that bringing in new talent earlier could have been beneficial for Digg's turnaround.
"We decided to sell the company and sell dig and ended up running a process and really working that process very thoroughly."
Matt explains the decision and process of selling Digg.
"We lost very few people on the team during that process, which I was very thankful and proud of."
He expresses pride in the team's stability during the sale of Digg.
"And then ended up having a couple of opportunities to be entrepreneur in residents and joined Andreessen."
Matt shares how he transitioned to becoming an entrepreneur in residence at Andreessen Horowitz.## Entrepreneur in Residence vs. Investment Analyst
I think it's different for every vc and I think it is what you make of it.
This quote emphasizes the flexibility and self-directed nature of the Entrepreneur in Residence role, contrasting it with the more structured role of an investment analyst.
Well, I think it's probably the single biggest takeaway is just simply the people that I worked with.
Matt Williams attributes his learning and growth to the influential people he worked with at major tech companies, highlighting the importance of teamwork and mentorship in his career.
Highlight of my career was selling my company at the age of 27 and being a part of a much larger business and picture at Amazon.
This quote reveals a defining moment in Matt Williams's career, underscoring the significance of entrepreneurial success and integration into a larger corporate structure.
Well, the vision is to build the best place for customers to find kind of book and pay for any local services.
Matt Williams outlines the future objectives for Pro.com, emphasizing the ambition to revolutionize the local service marketplace by enhancing customer experience.
What an amazing interview, delving into the career of a true legend of the technology industry.
Harry's closing statement encapsulates the significance of the interview and the impact of Matt Williams's career on the technology sector, while also directing listeners to additional resources and encouraging engagement with the show.