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

Summary Notes


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.

Summary Notes

Founders Friday Introduction

  • Harry introduces the segment Founders Friday.
  • Matt Williams, a notable figure in the tech industry, is the guest.
  • Matt has a history of founding Livebid, working at Amazon, being CEO at Dig, and serving as entrepreneur in residence at Anderson Horace.
  • Matt co-founded Pro.com in 2013, which is backed by Jeff Bezos and 16 Z.
  • Harry also mentions his new show in collaboration with Syndicate Room called Angel Insights, focusing on angel investing.
  • Harry requests feedback on the new show and Founders Friday.

"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.

Matt Williams' Background and Entrepreneurial Journey

  • Matt Williams is the founder and CEO of Pro.com, a marketplace for homeowners and professionals.
  • Pro.com has been publicly available for a year and in business for two years.
  • Matt's previous roles include being an entrepreneur in residence at Andreessen Horowitz, CEO of Dig, and a long tenure at Amazon.
  • He founded Live Bid at 23, which was later acquired by Amazon, offering a significant return to investors.

"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.

The Genesis of Live Bid

  • Live Bid started as a web technology shop, creating various products for different industries.
  • The company pivoted to focus on the auction space, building a real-time engine for online bidding in physical auctions.
  • Live Bid amassed $100 million in inventory offered through auctions within a year.
  • The success attracted acquisition interest from eBay, Yahoo, and Amazon.

"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

  • Matt Williams describes how they acquired their first auction items through partnerships and connections to auctioneers.
  • They had a small direct sales team targeting unique and hard-to-find items, including classic cars.
  • They successfully sold the Batmobile from a Batman movie online.

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.

Challenges and Overcoming Adversity

  • Live bid faced difficulties, especially concerning funding and management.
  • The company was self-funded with a small amount of seed capital.
  • Matt Williams faced pressure from his advisory board to shut down due to difficulties in raising capital and personal financial strains.
  • Despite the challenges, they found product-market fit with auction events, leading Williams to take charge of capital raising.
  • He successfully closed an oversubscribed funding round and hosted a high-profile auction event, the OJ Simpson estate sale.

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.

Advice for Founders on Funding

  • Matt Williams advises new founders to bootstrap until clear traction and product-market fit are demonstrated.
  • He emphasizes the importance of timing, market opportunity, and having a track record for more experienced founders seeking funding.
  • The advice includes getting feedback from VCs outside of fundraising contexts and demonstrating a strong team and product for seed rounds.

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.

Transition from Startup to Amazon

  • The acquisition by Amazon marked a significant change in the work environment and corporate structure for Matt Williams.
  • He does not provide specific details about how his life and work changed after the acquisition.
  • He suggests that founders considering selling to large corporations should carefully evaluate the implications.

No verbatim quotes provided for this theme.

Sale of the Batmobile

  • The Batmobile was sold for around $230,000 to $240,000 in 1998, which was significant for online sales at that time.

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.

The OJ Simpson Estate Sale

  • The OJ Simpson estate sale was one of the largest auction events broadcast online by the company.

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

  • Matt Williams began his career as a business analyst and evolved into a tech leader within NCR Corporation.
  • He taught himself programming and developed company-wide tools at NCR.
  • Matt comes from an entrepreneurial family with ventures in radio, education, and construction.
  • He emphasizes the importance of gaining career experience before pursuing entrepreneurial ventures.
  • There are similarities between being an entrepreneur and an intrapreneur, with the main difference being the environment.
  • Matt suggests that entrepreneurs can fit well within innovative and inventive companies like Amazon.
  • He notes that few founders stay long after their startups are acquired, but he stayed at Amazon for twelve years post-acquisition.

"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.

Experience as CEO of Digg

  • Matt Williams took over as CEO of Digg when the company was struggling.
  • Digg was once a top news website with over 40 million monthly visitors but had stagnated.
  • He faced immediate challenges with financials, headcount, and community dissatisfaction.
  • Matt had to make tough decisions, including laying off 40% of the staff.
  • He reflects that in hindsight, he would have brought in new talent sooner to inject fresh perspectives and drive.

"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.

Transition to Andreessen Horowitz

  • After deciding to sell Digg, Matt Williams managed the sale process and secured returns for investors.
  • The team remained largely intact during the transition, which Matt is proud of.
  • Post-sale, he had opportunities to become an entrepreneur in residence and chose to join Andreessen Horowitz, which had been an early investor in Digg.

"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

  • Entrepreneurs in Residence (EIRs) have different roles depending on the venture capital (VC) firm.
  • EIRs may have a desk and determine their next steps or engage directly with portfolio companies.
  • They can evaluate new investments, undertake projects, and assist with decision-making in the VC firm.
  • Matt Williams spent time at Andreessen Horowitz working with consumer portfolio companies and running data-related projects before starting Pro.com.

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.

Learning from Titan Tech Companies

  • Working with remarkable individuals and leaders is the single biggest takeaway from past experiences.
  • Close work with Jeff Bezos at Amazon and Ben Horowitz and Marc Andreessen provided invaluable insights into product development and company building.
  • The high caliber of teams at Amazon and Andreessen Horowitz set a standard for talent and innovation.
  • These experiences have significantly influenced Matt Williams's approach to running Pro.com.

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.

Career Highlights and Advice

  • The highlight of Matt Williams's career was selling his company at age 27 and being part of Amazon.
  • Advice to his younger self would be to maintain determination and drive when starting a company.
  • His favorite book is "Good to Great" due to its data-driven analysis of successful companies.
  • Ben Horowitz's blog is his preferred reading for insights.

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.

Future of Pro.com

  • The vision for Pro.com is to create the best platform for customers to find, book, and pay for local services.
  • The initial focus is on services related to home, aiming to improve transparency and ease of access.
  • The goal is to simplify the process of booking and paying for local services, addressing current market gaps.

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.

Conclusion and Resources

  • Harry concludes the interview, praising Matt Williams's contributions to the tech industry.
  • Resources and items mentioned in the show are available on the podcast's blog.
  • Harry invites feedback on the new show "Angel Insights" through email or Twitter.

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.

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