20VC: Why Venture Fund Life Cycles Do Not Align To Companies Today, Actionable Strategies To Separate Good From Great When Assessing and Hiring Multiple Candidates & Why We Need More Adventure in Venture Capital with Blake Scholl, Founder & CEO @ Boom Sup

Blake Scholl is the Founder & CEO @ Boom Supersonic, the world's fastest commercial aeroplane, aspiring to bring back supersonic passenger flight at an affordable price. To date, Blake has raised over $166M in funding with Boom from the likes of Paul Graham, Sam Altman, Ray Tonsing @ Caffeinated Capital, Homebrew and 8VC to name a few who have featured on the show in the past. Prior to changing the world of commercial flight, Blake started his career with a 5-year stint at Amazon as a Manager of Social Networks and Automated Advertising. Blake then went on to found his own company, Kima Labs, acquired by Groupon in 2012 where he then spent 2 further years before founding Boom. In Today’s Episode You Will Learn: 1.) How Blake made the move from Groupon to changing the way we think about commercial travel today with Boom Supersonic? 2.) How was the fundraising process for Blake given he was raising for supersonic jets? What is his most memorable fundraising moment? Where does Balek believe investors provide outsized value? Where could the investing class improve? How should the fund structures today change? 3.) What deliberate choices and decisions has Blake made to find and acquire the best talent? What is Blake's favourite interview question? What works? What does not work? What specific elements has Blake built into the culture at Boom to build operational excellence? 4.) How has Blake seen himself evolve and develop as a leader over the last few years? What have been the most challenging elements to develop and scale? How does Blake feel on whether founders should have experience on the industry they are entering or if there are benefits of not having so? 5.) What would Blake really like to change about the world of tech and Silicon Valley today? How does Blake feel about the current level of both innovation and founder ambitions? What can be further done to foster this in the coming years? Items Mentioned In Today’s Show: Blake’s Fave Book: Atlas Shrugged As always you can follow Harry, The Twenty Minute VC and Blake and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

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

• 0:00Harry Stebbings?

  We are back. This is the 20 Minute VC with me, Harry Stebbings, and I'd love to hear your feedback on the show. And you can reach me directly on Instagram at H Stebbings 1996 with two Bs. And I really do love to see you there. However, to the show today, and I've wanted to do this episode for a long time, particularly because this company is just so cool. And I've heard so many good things about their incredible founder, and I'm delighted to welcome him to the hot seat today. And so with that, thrilled to welcome Blake Shoal, founder and CEO at Boom Supersonic, the world's fastest commercial airplane aspiring to bring back supersonic passenger flight at an affordable price. To date, Blake has raised over $166 million in funding with Boom, from the likes of Paul Graham, Sam Altman, Ray Tonsing at Caffeinated Capital, Homebrew, and a dear friend of mine in Josh Buckley, to name a few, who featured on the show in the past as well. Prior to changing the world of commercial flight,

• 0:45Harry Stebbings?

  Blake started his career with a five-year stint at Amazon as a manager of social networks and automated advertising. Blake then went on to found his own company, Kima Labs, acquired by Groupon in 2012, where he then spent two further years before founding Boom. I'd also have to say a huge thank you to Josh Buckley and to Ray at Caffeinated for some amazing question suggestions today. I really do so appreciate that, chaps. But before we move into the show today, I'm sure you've heard about it, but my word, this is a product I love, Carter. Carter simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carter to manage hundreds of billions of dollars in equity.

• 1:27Harry Stebbings?

  And Carter now offers fund administration, so you can see real-time data in the Carter platform and work with Carter's team of experienced fund accountants. Simply go to carta.com/20vc to get 10% off. And speaking of managing the admin of those employee equity packages, well, do you already have a job? On Wanted, you can set the salary for which you would consider another job. Wanted is free, and there are only two steps required. One, you set your salary. Two, you submit your LinkedIn profile or resume, and that's it. Wanted will then reach out when there is an opportunity at this salary or more that matches your skills and experience. And Wanted already has over 50,000 talented individuals on the platform, and is used by the fastest-growing and coolest startups in the US. So don't waste time and energy.

• 2:10Harry Stebbings?

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• 2:51Harry Stebbings?

  and get card fees waived for life by entering the code HARRY during signup. But that's quite enough from me today. I'm very excited to hand over to Blake Shaw, founder and CEO at Boom Supersonic.

• 3:07Speaker 01

  You have now arrived at your destination.

• 3:10Harry Stebbings?

  Blake, my word, I've heard so many great things from Ray Tonsing, from Josh Buckley. It is such a pleasure to have you on the show today. So thank you so much for joining me today, Blake.

• 3:18Speaker 02

  Thanks for having me, Harry. Excited to chat.

• 3:20Harry Stebbings?

  I would though love to kick off today with a little on you. So talk to me, how did you make your way into the world of startups? And no offence, Blake, but it's very rare I have a company quite like Boom on the show. So how did you come to the idea of founding Boom and changing the way we think about travel and flights?

• 3:32Speaker 02

  Well, startups have been in my blood for a long time. I started my first company in my parents' basement when I was about 15. That was a tiny internet service provider. So I've wanted to start things virtually my entire adult life. And my first company, Chemo Labs, was a mobile e-commerce company that was acquired by Groupon. And I look back at that experience and one of my biggest learnings was that startups are hard. Even things that are theoretically in your wheelhouse are going to have challenging moments. And if you want to be successful, you have to think about your personal motivation and pick a mission that you will never, ever give up on, no matter how hard it is. So aviation has been something that's been in my blood for a long time. I've been flying for fun since I was in college,

• 4:12Speaker 02

  although I had a first career doing internet things and didn't really think about bringing aviation into my career till my mid twenties. And in 2007, When I put a Google alert on supersonic jet because I wanted to be first to know when I could go buy a ticket and go Mach 2. But for the better part of a decade, it was crickets. There's just no credible effort to build a supersonic aircraft that I could see myself or friends and family flying on and benefiting from. So after having left Groupon, I wanted to work on something more impactful than internet coupons. And I wanted to work on something that would keep me very motivated. So I organized all of my ideas by how happy I would personally be if it worked and neglected everything else. And I figured I would work down that list and work on the most exciting thing that was not impossible. And as luck has it, still working at number one on that list.

• 4:56Harry Stebbings?

  I mean, I love that in terms of tying happiness to the idea itself. I do have to ask, you mentioned Groupon, you also spent time at Amazon. In terms of kind of formative to how you think, both incredible companies. How do you think that your time there impacted how you think about operating with Boom today?

• 5:09Speaker 02

  It was incredibly valuable to spend time at both companies because they are ostensibly have some similarities, but have some really deep cultural differences. And one of the best ways to learn is to experience contrast. Amazon, as we all know now, is an insanely well-run company. When you work there, especially if it's your first job out of school, like it was for me. It's like the sky is blue, you can't actually see the background, you just take everything in the culture for granted. But having seen the contrast, one of the things that pops most is the importance of building long-range thinking into your culture and building a place where you optimize for the long term, not for the next quarter. And it was very interesting to watch how those two different companies would respond when there were short-term trade-off pressures.

• 5:49Speaker 02

  For example, if there was a supplier that was offering short-term discounts because they were having a soft quarter. In order to get Amazon to stock up on a product, like Amazon would take that deal if the long-term cash flow forecast was positive. And so they would allow earnings to be lumpy in the short term in order to have long-term good cash flows. And Groupon honestly was very much the opposite. If a quarter was coming in soft, the response was often to, hey, send more email. It will pump up the short term, but it's a little bit like eating your stock seed because it burns up your core customer base.

• 6:18Harry Stebbings?

  I had someone say to me the other day, Harry, the big lesson I have from 10 years in venture is the best startup founders have the ability to really operate and inspire at 5,000-foot level, but also go down into the granular. Really into the nitty gritty of cash flow optimization, whatever that granular might be. Would you agree in terms of the ability to transition between super high and super low in terms of being the best founders?

• 6:40Speaker 02

  I think that's totally correct. I mean, to be an inspiring founder CEO, you have to be able to zoom out and you know, really to the 60,000 foot level at Boom and see around corners, see around big obstacles, inspire people to continue to pursue the longest range vision in the most principled way, regardless of the short term obstacles in front of you. But you also have to go zoom in and enforce high standards and have great attention to detail. And that means everything from being willing to zoom in and edit marketing copy yourself, to auditing what the layout of the airplane will be, to digging into the details of what the QA process is on the airplane and making sure that every decision is appropriately geared to the right safety risk balance.

• 7:19Harry Stebbings?

  Yeah, I totally agree in terms of that ability to move between. I do want to ask about the topic of fundraising because it is such a unique company, which means I'm sure there's a unique set of experiences in terms of the fundraise itself. How was the fundraising experience for you, given you're essentially building supersonic jets? This is not an enterprise company. And can you share some memorable moments or elements that stood out for you?

• 7:39Speaker 02

  Fundraising has been incredibly challenging, yet I'm super excited about the success we've had. We've raised now a bit over $150 million from some of the best investors in Silicon Valley and really around the world. But it has been an arduous process. The very first seed round, I started by calling the people who had invested in my first company and made money in that, including people who had said, Blake, we'll invest in anything you ever do. And some of them wrote checks, but some of them were like, well, we said we'd invested anything you'd ever do, but we didn't think you'd do something this crazy. So we found the people who are willing to do it. We found the people who were excited about the vision. He would say things like, we think you're probably crazy, but I'd really love this to work. So here's 25K. And that was the start of it. And over a series of rounds, you get better at telling the story and you get better at reaching the people who are very long-term minded.

• 8:23Speaker 02

  And that in particular has been one of the most interesting challenges is Boom is a company that will probably be on the order of 10 to 15 years from founding to carrying passengers in volume. And that time horizon, even though the IRRs and the multiples will be great, makes it an impetus mismatch. For most venture capital funds in the early stages. And so a lot of our capital, as the company was particularly on the young side, has come from ultra high net worth individuals. Many cases, well-known VCs who are investing outside of their funds where they don't have those timing constraints. And then as the company has matured, we've been able to bring in strategics, a bit more institutional capital.

• 8:58Harry Stebbings?

  Can I ask, a lot of VC value add is centered around VCs being able to see around the corner, see that change management is going to be a real problem in this enterprise company and that we should really focus on investing in customer success upfront, six to nine months ahead. Given this is such a different proposition. A question from Josh Barclay. What do you find most helpful about your investors? And what do you think VCs, I guess, could do better and improve?

• 9:19Speaker 02

  So Boom substantively is very different from a software as a service company or your typical Silicon Valley startup. But company building is really the same regardless of what you're doing. You have to build an executive team, you have to build a culture. And those things pattern match very well across sectors. And so being able to talk with investors about how you build a culture, about how you structure an executive team, how you prioritize short term versus long term, how to time a fundraise, all those kinds of things. Our backers have been insanely helpful. And I feel really honored, like the quality of the people who are kind of watching Boom, who have invested in it and will send me an email when they think we're making a mistake and give advice proactively is just phenomenal.

• 9:54Harry Stebbings?

  In terms of where they could improve, help me out. I'm a VC by day for my sins, Blake. What could be better as like an asset class in terms of providing service and structure to you?

• 10:03Speaker 02

  I think the biggest thing that stands out is being able to structure funds so that you can make longer time horizon investments. That's the biggest reason that fundraising for Boom had been challenging is that timeline to exit is long, even if the multiples are going to be great. And that causes some funds to sit on the sidelines. So lengthening funds and focusing on multiples and IRRs instead of just your timeline to exit would be super helpful. And then I think there could be more venture and venture capital. The industry as a whole pattern matches very strongly on exactly what successes have existed previously. So for example, for today, it's really easy to raise money for a rocket company because SpaceX is a success. But that doesn't strongly translate over into aerospace as much as you would hope it would. I'd love to see longer time horizon investments. I'd love to see more venture, more willingness to try new concepts.

• 10:48Harry Stebbings?

  Can I ask, in terms of The meetings that you had, you obviously don't always get the money and people sometimes say no for whatever reason. Which individuals didn't invest, but did you really like and admire? And I guess, what did you like so much about those interactions?

• 11:00Speaker 02

  So I can think of many amazing conversations. It was very typical that we would make it to the full partnership stage and the fund would end up passing. Although individual investors in that group would come in personally. I think of one full partnership we had where the conversation was super amazing, incredibly engaged group. And then you get the call back after the meeting and they say, well, at this fund, we score every deal one to 10 before we have a debrief discussion. And this really strange thing happened, which was you got only ones and tens and nothing in the middle. And the partnership can't figure out what to do with this deal, but amongst the 10 group or a couple of well-known investors. And they want to do the deal personally, so you should do that.

• 11:37Harry Stebbings?

  I mean, I think that your answer to that should be the best deals are contrarian and tens and ones mean you should write me a check right now. But I love that in terms of the feedback. I do want to dive a little bit more into the leadership, so to speak, of the team and for you. I guess, you know, first when we think about building the team itself, we have to acquire the incredible talent. You mentioned culture there and helping in terms of building culture and how VCs do that. What deliberate choices did you make to attract the best and brightest talent, Blake?

• 12:00Speaker 02

  So culture, you do have to be very deliberate about and culture is bespoke. The culture at Apple is good at solving some kinds of problems. It's very different from the culture at Facebook or the culture at Google. And so when you're building a culture, you want to think about what are the attributes of a culture that are going to be necessary for succeeding at your goals? And for Boom, we're working on something that is incredibly long time horizon that requires a great degree of perseverance through the inevitable ups and downs. And so we chose to optimize for mission, passion as the fundamental tenet of our culture. And so we look for people who were as excited about supersonic flight as I am. We're incredibly committed to the mission of making the world more connected, making Earth a smaller place. And that's a filter even on great technical talent.

• 12:46Speaker 02

  If you're not excited enough, we don't hire you because it's too hard. And if you're saying you're going to give up somewhere along the way. So that was first and foremost a filter. And second, we systematically search the world for the best and the brightest, especially in the early days. I had No connection is all in aerospace. My best intro was a guy who had worked for me at Groupon, had played hockey in college, was someone who now worked at SpaceX. And so that was my first meeting. And I showed up to that meeting in an airplane I flown myself, which is my only source of cred in the industry at the time. But the question I asked him was, if you could wave a magic wand and get anyone on the planet to come be in the trenches with you to help you build this, who would you want? And he gave me five names. And then I met those five people and asked them the same question. And if you do that recursively, systematically searching for the best people on the planet,

• 13:31Speaker 02

  pretty quickly, you could actually be talking to them. And so of that initial five people, two of them now work at Boom, and people we met through them were also part of the early team. So you can search the world for the best and the brightest recursively. And when you're building supersonic jets, the first question people ask you is, are you crazy? And if you can convince them, the answer is no. The second question is, how can I help? So if you're working on something big and inspiring, you have the fundamental strength you need to attract really great talent.

• 13:55Harry Stebbings?

  Can I be super honest and open? And it's one thing that I struggle with today is when, obviously, VCs help in terms of hiring and winning talent. When assessing like CTOs, I find it fundamentally challenging not being an engineer myself. You mentioned your lack of experience in the domain specificity of space and supersonic travel. How do you analyze effectively the quality of roles where maybe you don't have the domain expertise? And I guess what advice would you give me, Blake?

• 14:17Speaker 02

  So I can tell you a story of how we hired the first couple of people because we had exactly that problem. I had spent a year self-educating, reading textbooks, taking airplane design classes. So I knew enough to be dangerous, but I didn't know everything myself. And so we had gotten to the point in early 2015 where we had a half a dozen candidates for the first couple of jobs in the company. And what I did is I flew them all out to the Bay Area, where I was living at the time. And I convinced a friend at Sequoia Capital to loan us a conference room for a couple of days. And we did a jam session with all of the candidates together in the room at the same time. And you might not know all the questions to ask yourself, and you might not know all of the answers. But if you get a group of smart people talking about your problem space together in a room, you can quickly tell who really knows what they're talking about. And also, who has the personality and ability to lead in a room

• 15:01Speaker 02

  that you really want to go get in the trenches with. And so out of that half a dozen people, we hired two and a third as a consultant to the company now. And just watching smart people interact With each other outside of your own domain, you can learn a ton. So that's that's story number one.

• 15:14Harry Stebbings?

  Could I ask just on that? Sorry, I'm too interested. Do you drive the conversation there and set the discursive threads? Or do you let them have their own discussion and really kind of observe from the outside?

• 15:23Speaker 02

  Some of both. So I drove the agenda. So day one was a jam session on everything technical. What would you need technically to make this work? And what was the current state of the art? What technology would need to be created? What already existed? And so the structure and discussion around that would bring out a lot of interesting things. And then day two was about company building and we asked questions like, should you start with a prototype? Or should you go straight into production? What do you look for in a great engineer? How is that going to be different in aerospace versus a software team? And so if you provide the right sort of structure and then let people riff on those questions, you're covering a lot of ground systematically, but also allowing people to take the conversation in places where you might not have thought of taking it.

• 15:59Harry Stebbings?

  Yeah, no, I totally agree. Sorry, the second, what was the second story?

• 16:03Speaker 02

  The second story is about interviewing and for the first 50 or so hires, my favorite interview question was teach me something. And so we were optimizing for people who not only knew deep technical things that mattered in aerospace, but were really great communicators. And that formed the foundation of a teaching culture and a learning culture. It also set me up for success because I would bring in people who were deep technical experts. We wanted to hire the ones who are not just good at doing what they do, but able to explain it to the team around them and teach people like myself. And so along the way, I learned a ton and if you couldn't teach me something, you didn't get hired at Boom.

• 16:37Harry Stebbings?

  I totally love that in terms of being able to teach and really express what you know. I guess my question to you is, we mentioned kind of the mission and the centrality of the mission earlier. We mentioned the talent, both especially kind of talent acquisition tougher than ever. You as the leader, a big thing that I think about now is kind of psychology of leadership. How do you manage the psychology of being CEO? And I guess, how do you deal with the shit hit the fan moments that are inevitable, but also more inevitable when it's a much longer timeframe in terms of the opportunity?

• 17:01Speaker 02

  I don't think there's a silver bullet answer to that. First and foremost is you optimize for your own motivation. And I spoke about that earlier. If you've picked something that really, really matters to you personally, then you're going to keep going no matter how hard it gets. And when you have a longer time horizon, one of the things that actually helps is you can anticipate that certain problems are going to come up at some point. And be prepared for them. Again, if you know it's going to be 15 years when you're founding an IPO, the chance that there's a macroeconomic event sometime during the lifetime of the company is basically 100%. And so you prepare for it. You make sure you always have more than a year of cash in the bank. And you have contingency plans for what would you do if the shit hit the fan? And that's something I've been preaching to the team for years now. And it feels very fortunate that we did that now with the coronavirus hitting,

• 17:43Speaker 02

  that we're able to say, great, well, good thing we planned for something happening at some point, and we're ready to weather the storm.

• 17:48Harry Stebbings?

  Totally. No, I do absolutely agree. I also do want to ask, you know, a lot of founders have the question of, is it better to enter an industry where you have this incredible domain expertise? And you've seen it all before? Or is it better to come afresh and have that kind of youthful naivety to address things in a fundamentally innovative and different way? How do you advise founders in terms of, especially your experience kind of coming into Boom without maybe the domain specificity that others have? In terms of whether to pursue something they know versus maybe don't?

• 18:13Speaker 02

  I think passion trumps expertise every time. And if you're smart and you're good at learning, you're going to be able to pick up a new domain relatively easily. I think people generally underestimate their ability to learn. And if you've got that excitement, you're going to be able to push through it. And there are benefits of being an outsider because domains often are littered with conventional wisdom that's false. A supersonic flight was like this. Six years ago, when we were starting Boom, the conventional wisdom was no one would pay enough to be able to fly supersonic, that it would have to be really expensive, that the sonic boom was an insurmountable barrier that would take decades of R and D to solve. And it turns out that basically all of that is false. It doesn't stand up to even a brief amount of systematic quantitative analysis. And an outsider who doesn't come burdened with that preconceived conventional wisdom

• 18:57Speaker 02

  has a huge advantage in being able to tackle problems that other people are ignoring. We have a saying at Boom, which is you have to be naive enough to start and wise enough to finish. So I think there's a huge benefit in going into something that's not in your domain expertise, within rapidly being able to burn down your naivete, understanding what assumptions you might be bringing that are false, and being able to get oriented rapidly in the new domain.

• 19:18Harry Stebbings?

  Can I ask for you as a leader, how do you think about giving people enough accountability and freedom to really pursue those big things that they want to achieve? But also creating a culture where it's okay to fail and they're not fearful of failing with that pursuit? That they've chosen.

• 19:30Speaker 02

  Well, we have something at Boom we call the blade and the nut. And this started from the earliest days of the company. It was about a five person company. And I had bought an engine blade out of Concord on an online auction just for fun. And I brought it into the company and it sort of became a trophy. When you did something really great, when you went above and beyond, you could have the blade. And we, you know, we put it on your desk until someone else did something amazing, then it would move. And along the way, somebody else brought in a nut on a rope. And they're like, if the blade is for when you do something really awesome, the nut is for when you really screw up. And I thought, oh no, this is horrible. The last thing I want to do is build a culture where people are shamed for their failures. We want to build a culture where everyone can own the mistakes they inevitably make. Or you're rewarded for surfacing problems quickly and then getting together with your teammates to overcome the setbacks.

• 20:13Speaker 02

  And this amazing thing happened while I was trying to figure out how to get rid of the nut. What happened was people started taking the nut when they own mistakes. And so it became you could be given the blade and you could take the nut. And so we have this culture here where you are rewarded for doing amazing above and beyond things. But you're also rewarded for owning your mistakes and learning from them. And so now that as the company has scaled, the nut has come to mean when something goes wrong, we understand the root cause. We talk to our teammates about it and we collaborate to recover.

• 20:40Harry Stebbings?

  I love that in terms of the blade and the nut. And that's fascinating in terms of the owning of the mistakes there. I do want to ask, because you've mentioned kind of the learnings from those mistakes. I spoke to many of your investors before the show and they said about your learnings as a leader and how you've really excelled in terms of scaling yourself. I'd love to hear, how do you see and how have you seen yourself change and evolve as a leader over the last few years, Blake?

• 21:00Speaker 02

  It's been a tremendous journey, building a startup. But by the end of it, you're not the same person you were when you started. I think it's toughened me a lot. I've learned how to be a better operator, how to operate at the right altitude, how to be able to helicopter up to the biggest level, but also get down in the details, how to do trust but verify, and how to get really good at the things that are critical for success in this business. Like I can share a little bit of a story. When I started the company, I couldn't recruit at all. I couldn't sell, I probably couldn't sell you a dollar bill for 50 cents. And I kept thinking about what would be the attributes of success for something like this to succeed? And we call it reverse historical reasoning. Like imagine yourself in the future, reading the history textbooks about how the world made the To supersonic flight and how do you think that story is going to go? Well, it's not going to be after 100 years of doing nothing. Boeing finally did it.

• 21:45Speaker 02

  It's probably going to be someone from outside the industry. And what would that leader and what would that team have to look like? Well, they have to have an incredibly long range perspective. They have to be incredibly perseverant. They have to have a really high talent bar and build a dream team. They have to be incredibly persuasive because they have to go convince airlines and suppliers and investors to all throw in with something that's very counterintuitive to go do. And so I said, well, okay, well, I got to get really good at recruiting. I got to get really good at fundraising. I got to get really good at sales. And again, it goes back to this idea of mission, passion, trumping everything else. And you have to decide you care more about the success of the company than you do about your own insecurities, about what you can and can't do. So then you go off and you run headlong into the things that you're afraid of doing. You pursue them anyway, and then you collect great mentors and advisors along the way

• 22:29Speaker 02

  who will tell you when you're screwing up and help you figure out how to do better.

• 22:32Harry Stebbings?

  Can I ask you a question? And it's a very personal one, but like I have many insecurities, especially kind of being younger in the industry. What are your insecurities today? Because everything can always look glossy and shiny from the outside. What are your insecurities today and what do you find challenging?

• 22:44Speaker 02

  One of the biggest challenges has been building an executive team in an industry that mostly doesn't have startups and a city that mostly doesn't have startups. So I think that's been the biggest challenge is how do you find big leaders who are cultural fits in a startup, but also have the deep expertise to be able to go lead big teams in aerospace? And we've made, honestly, we've made a lot of false starts on that. And it's been one of my biggest struggles. That said, as time evolves, as the company progresses, and now you can walk into our hangar and literally see the first airplane visibly in assembly. Our ability to go access big talent has gotten better. And our ability to go screen talent for culture fits is just something we've gotten wiser on over time. But that's been a big challenge for me personally.

• 23:26Harry Stebbings?

  I'm really interested because it's something that IT struggle with in terms of rising portfolio companies. How do you think about the balance between really maintaining someone and giving them the support, education and infrastructure to improve versus when to cut the rope and admit that it was the wrong fit?

• 23:41Speaker 02

  I think you have to look at people's slope of growth. Like, how quickly are they growing? How self-aware are they about their challenges? And the people who scale. Tend to be very humble. They tend to admit when they don't know how to do something. They tend to readily stick out advice. They tend to be great listeners and those folks grow really well. The pattern that I found doesn't scale really well is when there's a high degree of arrogance of self-confidence, thinking you already know the answer. Those people tend to get blindsided and are not able to scale when they encounter new things.

• 24:11Harry Stebbings?

  Now Blake, I do want to move into my favorite element of any episode, which is the quick fire answer. I say a short statement and then you hit me with your immediate thoughts. Are you ready to rock and roll?

• 24:20Speaker 02

  Let's do it.

• 24:20Harry Stebbings?

  Okay. So I'm sure you've read countless books. I'm struggling on this one. So help me. What's the favorite book and why should I be reading it?

• 24:26Speaker 02

  My favorite book of all time is Atlas Shrugged because it's one of the few books in which businessmen and innovators are the heroes. And it's got some amazing characters and stories of how they persevered to create new things despite all obstacles.

• 24:38Harry Stebbings?

  What's your superpower and then weakness in company building? 30 seconds on each.

• 24:43Speaker 02

  My superpower is being a strong futurist, being able to see around corners and paint a picture of how better the world is going to be. When we have supersonic flight, I'm really good at telling that story, inspiring people to want to go make it real. The flip side of that as a weakness is I run at problems that most people consider impossible. And sometimes that can make you unwise going and tackling something that is actually impossible. So it's a challenge to know when you're asking people to push and go figure out something they're going to succeed at versus when you're actually asking for a bridge too far and you're pursuing something that won't actually work.

• 25:16Harry Stebbings?

  What would you most like to change about the valley in tech today? You have this unique perspective of being in it, but also not being usual for it. What would you most like to change?

• 25:24Speaker 02

  I would love more founders to think about what they would do that no one else would do. So an organizing principle of my work is I only want to tackle problems that wouldn't get tackled if I personally didn't tackle them. And this is the opposite of a lot of the sort of herd mentality, trend focused mentality that you see in the valley where like, oh, crypto is big or video conferencing is going to be big and people like flood into the space. And I think about things like self-driving cars. It's going to happen. Lots of great people are working on it. Would it be fun to go work on? Of course, it's a cool, important problem. But regardless of whether I go into it, great progress. That's going to happen there. And so I want to look for the problems that are getting ignored, the things that might not get tackled if it weren't for one person's insight and decide to go pursue a problem.

• 26:10Speaker 02

  And I would encourage more people to think that way. Like, what can they do that no one else can do? What problem do they see that others are ignoring? I think there's a lot out there. There are a lot of problems that are sort of sitting in plain sight that have been largely ignored by the world, but people who see them and have passion about them can go do something.

• 26:25Harry Stebbings?

  Who was the first check-in to Boom and how did it come about?

• 26:28Speaker 02

  It was John Collison, the co-founder of Stripe. And this was in the relatively early days of Stripe before it was the massive success that it was today. John was a pilot. I met him through a friend and we went out to dinner. We're talking about what we were doing and why I thought it would work. And John is awesome. He said, well, I'll write you a check now if you can promise me that I'm the first one. And we said, of course, yes, let's do it. And he's been amazing to have involved. He is a brilliant operator, you know, comes out to Boom from time to time and kind of helps deep dive on things and coaches me. Amazing person to have involved.

• 26:57Harry Stebbings?

  Who's the biggest mentor to you and what's been the takeaway from that relationship?

• 27:01Speaker 02

  I'd say Jeff Holden. So Jeff hired me at Amazon, coming up on 20 years ago now, straight out of school, when he was running supply chain at Amazon. And I worked for him there. I worked for him at his startup again at Groupon and now he's on the board at Boom. And Jeff taught me how to think big. He taught me how to close, how to sell, how to persuade, and also how to be an amazing operator, how to dig into root cause, how to challenge your teams to do better. And I feel like I'm still learning a ton from him.

• 27:27Harry Stebbings?

  What's the hardest role to hire for today in your mind and why do you think that is?

• 27:31Speaker 02

  The hardest thing to hire for is big leadership roles that require aerospace background. And that is because the background is crucial for us to have. If you're going to go off and build overture, which is probably one of the most complicated, safety critical things ever built by humanity. You need to have people who have deep experience in building, certifying, testing a large aircraft. However, you also need people who can operate in smaller environments who are going to be culture fit at a startup. That is a very, very small set of people on the planet. And the good news is when we find the ones that fit, we're able to get them. But it's just not a big population today. And you know, one of my biggest dreams for Boom over the long term. Is we build what we call the talent distillery where we can bring in young spirits and help them mature and grow into future leaders.

• 28:16Speaker 02

  And I would love to see that challenge getting solved in the industry. If we can go create a lot of talent that understands startups and how to operate in startups, but also has a deep background in airplanes and therefore can go create a bunch of companies.

• 28:26Harry Stebbings?

  Speaking about the future there, probably the most important and final one, what are the next five years hold for you and for Boom? Can you paint that product roadmap?

• 28:33Speaker 02

  Yeah, so today we're building our first aircraft, the XB1, which will look like a fighter jet but fly like an airliner. And that is history's first independently developed supersonic jet. So that's literally coming together as we speak. The the wings were finished a couple of weeks ago. The fuselage came together earlier this week. Wings and fuselage together next month. So it's quite literally coming together in our hangar. So that airplane will be finished this summer. They'll be flying to set speed records next year. And from that point, we shift our attention from that prototype to the production aircraft called Overture. And so that airplane will carry 75 passengers at business class fares on flights that are half as long as they are today. So think, you know, New York to London in three hours instead of seven, you know, fast enough, you can go across the pond, get business done and be home to tuck your kids into bed.

• 29:15Speaker 02

  So that's going to be our major focus over the next five years. And it's a continual question of, okay, how do we build this to be safe? How do we build it to be sustainable, environmentally friendly, affordable to as many people as possible? And that's what we think about every day is how do we bring high speed travel to as many people as possible?

• 29:31Harry Stebbings?

  Blake, as I said, I had so many great things from many, many different people. This has been so much fun and I cannot wait to see the future ahead. So thank you so much for joining me.

• 29:39Speaker 02

  Thank you, Harry. Really enjoyed the conversation.

• 29:43Harry Stebbings?

  I just love that discussion with Blake and such exciting times ahead with Boom. And if you'd like to see more from Blake, then you can find him on Twitter at B Shol. Likewise, it'd be great to welcome you behind the scenes here. You can do so on Instagram at H Stabbings 1996 with two Bs. However, before we leave you today, I'm sure you've heard about it, but my word, this is a product I love, Carter. Carter simplifies how startups and investors manage equity, track cap tables and get valuations. Go to carta.com forward slash two zero VC to get 10% off. More than 800,000 employees and shareholders use Carter to manage hundreds of billions of dollars in equity. And Carter now offers fund administration. So you can see real time. Data in the Carter platform and work with Carter's team of experienced fund accountants. Simply go to carta.com forward slash two zero VC to get 10% off.

• 30:28Harry Stebbings?

  And speaking of managing the admin of those employee equity packages. Well, do you already have a job on Wanted? You can set the salary for which you would consider another job. Wanted is free and there are only two steps required. One, you set your salary. Two, you submit your LinkedIn profile or resume and that's it. Wanted will then reach out when there is an opportunity at this salary or more that matches your skills and experience. And Wanted already has over 50,000 talented individuals on the platform and is used by the fastest growing and coolest startups in the US. So don't waste time and energy on a recruitment process that takes months and yields a salary beneath your expectation. Get a raise on getwanted.com. And once you get that incredible talent through Wanted, they have to be properly equipped. And that's where Brex come in.

• 31:11Harry Stebbings?

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