It was an amazing pleasure to host Bill Bryant from Threshold Ventures on my show. To be honest, there was almost a sense of trepidation... not in a fearful way, but of respect. As I began to dig into Bill's history of success and perseverance, my respect for Bill began to rise. It was almost like a 30-minute conversation would be impossible to extract all of the learning, the wisdom, the knowledge. What hasn't passed Bill's desk over a 30+ year period in venture? What experiences has he not had?
Bill began his life in technology in Seattle, during a period when Microsoft was beginning its rise to dominance in the late 1980s. I could only imagine what it was like to be part of the select few, the small community of technologists or cypher-punks (about 30 or so from Bills estimation) gathering together from the MIT Enterprise Forum to talk about the newest hardware, software, or rumors of how the landscape is changing because of the new giants-of-tech were moving in. And remember, this was all pre-internet. BBS boards? Telnet? Not mainstream just yet.
Lucky for Bill, he knew that he wanted to be an entrepreneur since he was 12 years old. Even though he didn't exactly know what that meant, he was in the perfect place to leverage his passion and interests. The ecosystem just grew around him! What a blessing!
"I knew since 12 I wanted to be an entrepreneur. I just didn't know what that meant. I just felt that I wanted to do something on my own terms and carve out my own destiny and fortunately software arrived at the time I was entering the workforce and I was part of the Seattle technology transformation."Bill Bryant - VC Hunting S1E7
I especially enjoyed the fact that Microsoft Visio was brought up as a real pivotal moment for Bill in his career. I remember so fondly using that application (in it's more robust form) even though I never considered it a perfect application for showing process flows (When better templates came out, it got exceptionally better). As employee 19, Bill got the opportunity to really dig deeper into the technology space and watch desktop software pretty much die off after his time at Visio as Microsoft sucked all the air out of desktop applications with office and bundling and world-domination...
From 1988 to 2006, Bill jumped into many tech startups supporting a multitude of roles and in 2007 joined DJF as a Partner (Draper Fisher Jurvetson), which has now rebranded to Threshold Ventures.
"I'm sort of humble bragging here... but I have been involved in more successful Seattle software companies than anybody else. About 25 now to date."Bill Bryant - VC Hunting S1E7
As I responded, there's nothing wrong with just stating the truth, and Bill's track record certainly speaks for itself. On the topic of Bill's track record, I found it fascinating that he really isn't a thematic investor. While many funds have thesis/themes that they invest in (and this isn't a bad thing as Bill and I discussed later in the show), Bill's vision for investing really has been in great people and great hustlers. Coupled with the fact that the Seattle startup world just isn't saturated enough for theme-investing, I really appreciated Bill's honesty around he finds great people to invest in:
"I've done a ton of investing all across the gamut and there are two reasons for that: One is you can't be thematic in Seattle. There isn't enough of just one thing to just focus on other than enterprise software. Secondly, as an entrepreneur, what I'm looking for are these aspirational, visionary individuals who have spent the last months, years, to work out an issue or problem, I want to see the world through their lens and the motivation that's really driving them. That's what I really get excited about and I want to help them realize their own personal dreams."Bill Bryant - VC Hunting S1E7
My follow-up question around what Bill looks for in an entrepreneur may be table-steaks, and Bill's answer may sound similar to many other's responses... but I knew the deeper nuance to why Bill asks "why" of each founder he meets.
He clearly uses the question of 'why' to suss out the bs. To get to the heart of the person. To understand the deeper motivations behind just the idea. As we discussed later, intelligent people just figure out ideas!
"Building a company is extraordinarily difficult. So I want to understand the motivation and will this person push through, do they have the kind of grit needed. To be an entrepreneur is not a rational decision. There is something that's driving them internally and they just have to get this thing done, or life is failure. I really want to understand that."Bill Bryant - VC Hunting S1E7
Bill really enjoys the team-building part of startups and the mentoring and coaching of founders to greatness and to use his words, ensure that the founding companies culture is 'strong cultured' not 'weak cultured.' It was so apparent when he talked about it that I could tell that this type personal rewards for him enabled him to stay in the game for many years. I appreciated Bill's candor around being in the game for 30+ years, and enjoyed his sharing of the times when he was fired from his own startup and how we got through that, what learnings he had, and how it helped him grow as an individual. Make sure to not miss that part of the show!
According to a tech crunch article below, I wanted to verify whether Bill still invests in iconic and transformative companies... but the deeper question, which Bill immediately picked up on, was... how do you know if they are iconic and transformative... at the early stage?
Having met with over 10,000 entrepreneurs, the founders need to have a big idea. They also need to have a bit of traction as Threshold Ventures invests in early-stage, not seed-stage. Beyond that, Bill describes that entrepreneurs have to understand the game as well. VC's need to be able to match their vision with their expected returns on investment:
"Venture capitalists have a business model too, and the more that entrepenures understand what that business model is, the better they are at raising capital."Bill Bryant - VC Hunting S1E7
What a great reminder for all of us founders out there to be aware and cognizant that both side of the table have to feel great about the deal... before it's a great deal.
I can't wait to see what Bill has up his sleeve in about 45 days or so... He said something is brewing (and we know it's not Bitcoin), we'll make sure to get him back on to discuss in the next seasons!
Bill, I hope I did you a solid on this interview. It was life-giving indeed. Enjoy my retrospective:
All the best,
Keep that up, and I'll be hunting you next.
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