20VC: Alexa Von Tobel on Raising NYC's Largest Ever Female Led Fund , Portfolio Construction, Compression of Fundraising Timelines, Reserves Management & Personal Branding in Venture

Alexa Von Tobel is the Founder & Managing Partner @ Inspired Capital, announced in 2019 as the largest ever female-led VC fund based in NYC. Prior to co-founding Inspired, Alexa founded LearnVest where she enjoyed an incredible 11-year journey culminating in their $250M exit to Northwestern Mutual in 2015. Alexa is also the author of New York Times Bestseller "Financially Fearless" and is an inaugural member of the Presidential Ambassadors for Global Entrepreneurship for the White House. In Today’s Episode You Will Learn: 1.) How Alexa made her way into the world of startups with the founding of LearnVest? How did that experience running LearnVest lead to her founding NYC's largest-ever female-led VC fund in the form of Inspired? 2.) How does Alexa think about portfolio construction with the new $200M fund? What does she mean when she says they have segmented it into 3 distinct and separate buckets? How much is in each bucket? How does Alexa think about reserves and re-investment decision making? What is the process here? 3.) As a former entrepreneur, how does Alexa think about those moments when the VC and the Founder are no longer aligned? What are those moments? How does Alexa approach the aspect of saying no to founders? What is the right way? How does Alexa feel about the compression in fundraising timelines? How does Alexa meet founders before they raise their round? 4.) Why does Alexa believe that capital is no longer the differentiator? How does Alexa think about personal brand in venture today? Where does Alexa believe are the most crucial times for reputation building? How does Alexa approach time allocation across the portfolio? What is the correlation between decision-making and reputation? Items Mentioned In Today’s Show: Alexa’s Fave Book: The Power of Moments: Why Certain Experiences Have Extraordinary Impact Alexa’s Most Recent Investment: Snackpass As always you can follow Harry, The Twenty Minute VC and Alexa on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

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

• 0:00Harry Stebbings?

  This is the 20 Minute VC with me, Harry Stebbings, and I'd love to hear your thoughts and feedback on the show. Do ping me on Instagram at H Stebbings 1996 with two Bs. It would be awesome to see you there and I respond to all messages personally there. But to the show today and switching coast to the East Coast, and when I saw this fund announcement back in 2019, I knew this was a show that I would love to do, and so I'm super excited to welcome Alexa Von Tobal, founder and managing partner at Inspired Capital, announced in 2019 as the largest ever female-led VC fund based in New York. Prior to co-founding Inspired, Alexa founded Learnvest, where she enjoyed an incredible 11-year journey, culminating in their $250 million exit to Northwestern Mutual in 2015. Alexa is also the author of New York Times bestseller, Financially Fearless,

• 0:42Harry Stebbings?

  and is a member of the Presidential Ambassadors for Global Entrepreneurship for the White House. I'd also want to say a huge thank you to Satya at Homebrew, Rebecca at USV, and Alexa's partner Lucy for some fantastic question suggestions today. I really am grateful for that. But before we move into the show today, this episode is brought to you by Silicon Valley Bank. For over 35 years, Silicon Valley Bank has been the bank for visionaries of all kinds, people and businesses who've revolutionized everything from software to social media, from workspaces to wine. With nimble banking services and solutions, Silicon Valley Bank helps startups adapt to the changing needs of a growing company. Learn more at svb.com backslash next. That's Silicon Valley Bank, ideas bank here. Let's face it though, also, everyone not only needs banking, but everyone today wants to start a podcast.

• 1:27Harry Stebbings?

  But man, the incumbent toolset sucks for creating podcasts, take my word for it. And that's why I love Descript so much. Descript is the brand-new way to record, edit, and mix spoken-word audio. But for me, the main reason I just love it is because it takes your audio and it turns it into text. And so you can actually edit the text, almost as if it's a Word document, and remove the audio and the text that you don't want, and it's super simple and just the best tool that I've seen for editing by far. We love it here. And now with our team at 20VC also, Descript has this amazing live collaboration feature, so we can work on the edits in real time, so we can comment, people can agree, disagree. Honestly, if you want to master your new podcast, you have to use Descript for the process. And you can find out more at descript.com. They really- Have built something special, that's descript.com.

• 2:12Harry Stebbings?

  And finally, as a VC, our job is to find the very best companies before anyone else does. And as an operator, you have to know who your competition is and how they're doing. And that's where Spectre comes in. Spectre formerly called CrunchDecks. Essentially, do you want to know what is the fastest growing company in your city or vertical? Well, Spectre tracks 140 variables and growth signals from close to 17 million private companies worldwide and is a trusted partner to three out of the top 10 VCs. To learn more, check out trispector.com. That's trispector.com. But that is quite enough of this terrible English accent. So now I'm delighted to welcome Alexa Von Tobel, founder and managing partner at Inspired Capital.

• 2:58Speaker 01

  You have now arrived at your destination.

• 3:01Harry Stebbings?

  Alexa, my word, I've been solely forward to this episode for quite a while. I've heard many good things from Satya at Homebrew, from Rebecca at USV. So thank you so much for joining me today.

• 3:10Speaker 02

  Thank you. I'm so excited to be here. And as somebody who's listened to so many of your podcasts, just really pumped to be on, so thank you.

• 3:16Harry Stebbings?

  That is so kind of you to say, and I'm thrilled you like them. But I would love to start here with a little bit on you. So tell me, Alexa, how did you make your way into the world of startups? And make the transition into the weird but very wonderful world of venture and also founding Inspired?

• 3:28Speaker 02

  So I'll just say it started probably when I was 10ish years old. I was the weird kid that rather than like having lemonade stands, I would like take art off the wall. By the way, not fancy art, like just, you know, some art off the wall of my parents' house. And I would like sell it on the street and definitely did not make for being a great child. But I think it really early showed me I was an entrepreneur. Went to Harvard undergrad, started my career actually at Insight Venture Partners, where I gravitated right there early. And I quickly realized that I was obsessed with entrepreneurship. I was enamored with it. I was the kid who thought that CEOs were cooler than like pop stars. And I think I quickly in my early twenties realized that that was what I was excited to do. So a good friend of mine, Sam Lassen, was starting Droppio.

• 4:11Speaker 02

  I went over there early and got a full dose of what it's like to build a company. And that was 2007 in Dumbo. And then ended up going to Harvard Business School, dropping. Out had been working on a business plan for Learn Best and did the weird thing of starting a company at the bottom of the recession. And eventually Learn Best got acquired for about three hundred and seventy five million dollars. And through all of that, I realized I was just obsessed with entrepreneurs. I would help them for free nights, weekends. And as I started angel investing, it became clear to me that that's what I wanted to do next. After my own track record and history in my own entrepreneurship career.

• 4:46Harry Stebbings?

  I mean, there's so many things that I want to touch on there. First, all the best to drop out. So like, I'm thrilled to hear about that dropout. Second is Sam Lessin. I love this man so much. I've had him on the show about four times, poor guy. And then the third is, you mentioned the angel investing there, and it's a really interesting one for me. And one that I'm actually navigating the transition to now with our new fund is how do you think your mindset changed? Angel investing compared to institutional investing. It was actually Josh Koppelmann and Ali McLaughlin that said they became more conservative. How did your mindset change, do you think?

• 5:15Speaker 02

  Yeah, I mean, to think about it, when you're angel investing, you're a steward of your own capital. And that may mean you really like somebody, you give them some money, the return profile may be two X, five X, it may be lower. When you're running your own fund, you are steward of someone's capital. I take my fiduciary responsibility extremely seriously. My, as I ran Learn Best, I ran a regulated company, a registered investment advisor. I became a certified financial planner and I take the fiduciary piece so seriously. And so I think how it changes is you then think about what are my goals with this capital? And if your goals are to perform a powerful top decile fund, it changes, right? And as an angel investor, you may say, oh, I love this entrepreneur, they're on to something, but here's twenty five K.

• 5:59Speaker 02

  Versus I'm here and this is my full time job. And it just sharpens the investing pencils, I think, quite a lot.

• 6:06Harry Stebbings?

  Oh, I think it totally does. It's always a nightmare having to write an investment memo for the institutional checks. I do want to touch on the firm itself, though. We spoke about the institutionalization there. It's the largest ever female led VC firm in New York. So starting from a question from one of our mutual friends, Satya at Homebrew. He said, what was your pitch to LPs and why do you think it worked so well?

• 6:25Speaker 02

  Well, first I'll just say, we've got a lot of work to do. I really do think. That we have 20 years ahead of us of exceptionally hard focused work. And so it worked well in that we got into business very quickly, which is wonderful. But I really do feel like we're just getting started. And I think what resonated was, one, our team. So the group of people behind Inspired Capital. We've known each other for maximum 20 years, minimum a decade. And I think that that just really makes a really different chemistry in terms of the group of people. So Penny Pritzker, who was Secretary of Commerce, has, you know, six companies that she's helped build and scale and sell behind her belt. Mark Batzian, who I've worked with for a decade. He and I were the deal team behind Learn Best.

• 7:07Speaker 02

  We were running North Russian mutual ventures together after our acquisition. And then Lucy Deland, who was a co-founder of Paperless Post, who literally was my best friend undergrad at Harvard. We both were building companies at the bottom of the recession, her at Paperless, me at Learn Best. And she also worked at Inside Venture Partners. And so I think the DNA of our team there was, one, highly, highly tightly knit team of, we're quite different people, but exceptionally committed to excellence and entrepreneurship. We all started on the investing side and then migrated to the entrepreneurship side and then went back to the investing side. And I think that in itself is quite special. We're not just operators turned investors. We actually started on the investing side.

• 7:47Speaker 02

  And then once you really get to meet us, I think our passion and enthusiasm for entrepreneurship is real. It's authentic and it's stupidly committed. We would do it for free every single day. And between all of us, we have helped build and scale 10 major companies. And I think that's just, that's pretty cool and I think quite different.

• 8:05Harry Stebbings?

  I totally agree with you. And I also think for LPs, you know, one of the biggest concerns is always team risk, especially with the first few funds. And so given the nature of your incredibly tight knit relationships, kind of team risk is relatively removed. So I totally agree with you that.

• 8:18Speaker 02

  If we haven't broken up with each other by this point, we have been through so much. And I think, and by the way, we chose to be together and it's a really, I think that that is quite special. And then I think just last thing is we're in New York City. And I think we are the kids who are helping be part of the fabric of this ecosystem. As I mentioned back to Dropio, 2007 and Dumbo. I actually started Learn Best in a Starbucks and it was amazing. There was, there was no seed capital. And I think just having been part of the fabric of this ecosystem, we're just incredibly passionate about, you know, helping fuel more companies, both in New York and around the country. But again, we just have deep roots in New York.

• 8:55Harry Stebbings?

  So that's what worked well in terms of the fundraiser. If, if you're kind of maybe more self-reflective and critical of yourself, maybe. What do you think that maybe you didn't do so well? And what elements would you really like to improve about the pitch or the process of fun too?

• 9:07Speaker 02

  Well, I think just, and I don't know that I changed this. So my last day as I transitioned off the management team at Northwestern Mutual, the firm, literally the last day that I left Northwestern Mutual and launched Inspired, it was the same day. And on that day, we'd closed about a hundred and twenty five million. So it happened instantly. And then I had my baby, my, my baby girl, Rosie, she was born right after we launched. And I couldn't fly. So I like couldn't run a proper fundraiser because I literally couldn't get on planes. And so we kind of took a minute break and we kind of put our pencils down for ninety days just so that I could get organized. The, the full team was coming together. We got our back office set up. We got all of the logistics and the infrastructure set up. And then we finished the final seventy five million over the summer, ninety days.

• 9:51Speaker 02

  And I'll just say I couldn't change what was going on in my personal life. And so we fundraised in the middle of the summer, which I think probably any smart human would tell you, don't do it. But it was just for us, our reality. And so we did it and it ended up going really well. And, you know, we got everything wrapped up. But I would just say in general, like fundraising, do it in the beginning of the year when people are super focused. Do it in the fall when people are super focused. But we did it in the summer. And I think that just put a lot of logistical work on our plate. But again, we ended up getting it done.

• 10:19Harry Stebbings?

  No, totally. You didn't. I mean, incredible time there in terms of productivity in such a short time span. In terms of the actual management of it itself, we mentioned Sam earlier, and he also asked, as a first time fund manager, what's been the most surprising element of fund management for you?

• 10:32Speaker 02

  You know, as I said in the past, starting on the investing side, and then I was responsible for North Russian Mutual's venture fund. And so, nothing has surprised me because we were doing this prior. I think the one thing that we just think so much about really is that portfolio construction and being incredibly thoughtful about how we think about the math around the portfolio. And I think that's really critical on our Monday agenda. It's literally at the top front and center. We have like a full model that matches our pacing and where we are. And not because we need to follow it exactly, but it's more to just really make sure that it stays front of mind. I think that's one thing that I think a lot about and our team thinks a lot about. So yeah, I would say that's probably the thing that, you know, you think about it from afar.

• 11:15Speaker 02

  It's about ideas in the future and ideation and thesis building. But it's also really about, I call it the Venn diagram between the market, the founder and the deal. You need all three to come together and you need that tiny triangle between the three to be your bullseye when you actually decide to deploy capital into something.

• 11:32Harry Stebbings?

  I mean, that portfolio construction element is actually, as you probably know from listening to the show, one of my favorite topics to discuss. How do you think about that with 175 million then? What does that look like in terms of diversification, in terms of initial to reserves? How do you break that down in terms of the core mechanics?

• 11:47Speaker 02

  Yeah, so our fund is 200 million. So for a 200 million dollar fund, you know, we really do think about it as saving a sizable chunk, 50% for reserves, 50% for initial deployment. We almost then break that up into three smaller funds inside our own fund. We think about them very formally and very separately. And I think that again is more about our process and our decision-making rigor. And then we essentially think of it as we have an early-stage seed fund, where we think about big, big, big contrarian, wild ideas with founders we're really passionate about and take the time to get to know. And in that portion, we'll bet on an entrepreneur with an early napkin idea to a true kind of seed deal.

• 12:30Speaker 02

  And then the majority of our capital really goes into that second bucket, which is that I'm going to call it a Series A, but I almost think we need to get rid of names because I think in this environment, some Series As look like Some Series As look like seed extensions, some Series As are real Series As of the decade ago when I was building LearnBest. And I think of it more in terms of progress of the company, de-risking of the asset on that spectrum. So, Series A. And then our third kind of portfolio, if you will, is really our follow-on. And that has its own rules and operations of how we think about it coming back to committee. So, that's a bit how we actually think about it in practice.

• 13:06Harry Stebbings?

  I absolutely love that segmentation. I'm so glad we asked this question. Can I ask, are the buckets equal between the three for the first initial checks?

• 13:13Speaker 02

  No. So, obviously, our pre-seed checks are smaller, our core Series A checks are, you know, where we'll write our bigger checks. And then, you know, we almost think about our follow-on as our own mini opportunity fund inside our fund. Again, for rigor and for practice and for portfolio construction. And obviously, that depends upon how the company's tracking and what follow-on should look like and valuations, and that's so specific to the deal.

• 13:36Harry Stebbings?

  Totally. Can I ask, how do you determine and what does the reinvestment decision-making process look like? Because it's always a tough one. How do you think about optimizing that?

• 13:44Speaker 02

  Yeah, and so keep in mind, our portfolio is months old, so it's very, very early. We haven't had to go through anything just yet there. And I think the way that we really do think about it is going to be dependent on each of the companies. We obviously want to be supportive of our companies in every way, and I will just pause on that. Having been in the seats of the founders, I would say one thing that, and lots of great funds, you know, all of the funds that I admire, and I admire so many great funds out there, have CEOs and operators as part of their team. And knowing that we kind of are overweighted on being founders ourselves, we just bring so much sincere empathy to that because we've been those entrepreneurs. And I remember the phone calls of being like, are you going to support my deal? What does Prirata look like?

• 14:27Speaker 02

  I remember those phone calls to this day as though they were yesterday. And so, you know, I think about, we care deeply about always being really, really supportive, being really transparent of helping the entrepreneurs and what that will look like. And then, you know, we're inclined to always be as supportive as we can. That said, portfolio construction is you can't spread your capital like peanut butter. And so, I think that is, gives you a sense of how we think about it, which is you really want to triple down on your winners when companies are doing exceptionally well, help get ahead of. I like to take fundraising when I can off the founder's plate to say, hey, listen, this is going well. Let's just go quickly pull together more capital so you can keep your head down. Because once you're in the flow of really executing, you want to stay in that flow. It's a mindset. You want your head down. And so, where we can actually go and lean into helping our entrepreneurs, we want to do that.

• 15:11Harry Stebbings?

  Can I ask, do you find out, I'm sorry, we're quite off schedule here, Alexa, but as I said, I like.

• 15:15Speaker 02

  I love it. I love it. I'm like, go, go for it. I listen so much. I feel like I could talk to you for five hours.

• 15:20Harry Stebbings?

  Well, you are such an innate entrepreneur and there are moments and everyone will say about founder and resealignment and absolutely it's nineteen five percent of the time, if everything works, it can be like that, but there are some times where maybe you want to lead a reinvestment round and there's a moment where you're pricing the round. For you, is it difficult, having been a founder and being such an innate founder, when there is that moment of, well, I'm an investor now and I'm a shareholder and it's not optimal for me to give them that price. I'd like to cram it down to this price because that's optimal in terms of my ownership. Is it difficult switching hats and having those sometimes moments of misalignment?

• 15:55Speaker 02

  No, I actually, and I don't even think that, and maybe this is too optimistic of me, but I don't even think that those are moments of misalignment. And let me be clear, venture returns are not made on like a few million dollars evaluation. That in the end, it's about picking the breakout companies that are the category creating businesses of the next decade and making sure that you are at the table in a handful of those. I think in those moments of like, I actually feel deeply aligned to the entrepreneur and again, maybe this is just my vantage point, but one thing I often say to the entrepreneurs is, hey, listen, in the end, often it's founders, you know, sole founder, double founders, whatever it may be. I say only one thing truly matters here and it's you in a decade.

• 16:37Speaker 02

  And I often say it's a decade because start to finish for learn best, it was really about seven and a half years. Most of the times it's about a decade and I say to them, in a decade, we want to have the biggest exit that we humanly can. And that's how I approach it. And I say, one thing matters is the W at the end of this. And we want to every day come to work and make great decisions. And so it's about every decision being a little bit up and to the right. And so again, if a founder is in that position, I'm like, I'm not looking to get the squeeze of the absolute best valuation and they shouldn't either, right? It should be somewhere in the middle where it's sensible and thoughtful so that you can constantly keep building a great business. I think one of the things that worries me in the environment today is sure, you can get away with wild valuations. There's a lot of capital out there.

• 17:21Speaker 02

  In fact, capital is not the differentiator, but only one human really holds that valuation, and it is the founder. It's the person who's at the helm of steering that company to success. And for them, I always say, you're actually doing yourself the best interest to go out and get a fair valuation, not the maximum and not the minimum, a fair one, whatever that may be in the middle. And so that's why I do believe that for the fund, for the investor and the CEO, you actually are quite aligned if you really do take deep, thoughtful, long-term views. And one last thing I'll just add to that. When I was building LearnBest, there were times where I backed our Series B and Series C, where I could have pushed the valuation by about another $50 million. But I always had this spreadsheet in the back of my mind, and it literally was a spreadsheet,

• 18:03Speaker 02

  of every single potential acquirer out there who could hypothetically ever be interested in LearnBest. And I didn't run it because we were building a company to get acquired, but I need it as like a sense-making system to make sure we never went over our skis. And the truth is, like, there's acquirers who can buy something at 100, at 300, at 500, at a billion. And as you go up on those ladders, the number of acquirers go down. And so pushing it too fast into a realm where you really are beginning to limit the outcome for the company, that's not great for the investors. But most importantly, it's not great for that founder that is going to live and breathe and sweat that business for a decade, every night, the sleepless nights that they will carry. And so that's how I kind of approach it. And I think it's about like, let's get to a reasonable place.

• 18:44Harry Stebbings?

  I mean, I think we could literally chat rages on this thread, but I want to, I want to dive a little bit deeper because you said about the excess capital there. And I can just, as I said earlier, you can tell you're an innate entrepreneur just from listening to you. Do you find it tough today, because I find this tough, with such excess capital, funding rounds are so much faster moving than in my eyes they ever have been. Do you find it tough to really build that founder relationship in such compressed timelines? And does that worry you?

• 19:08Speaker 02

  Yeah, but I think it's a little bit of our approach of how we think about it, which is, and again, maybe this is like incredibly stupid how I think about it, but the absolute truth is, I signed up to do this job for the rest of my career. And I am a complete, I, you know, I love to work. I've kind of come to terms with like, I don't have hobbies, like this is my life. It's my hobby, it's everything outside of my family and friends. And I really approach building relationships with Entrepreneurs as just like everyday community building, plan to live in this ecosystem in New York for a really, really, really long time. And so we often go for fun to like go meet people pre-thinking through ideas. I, once a month, have a dinner where people come over to my apartment and we just totally with zero agenda, talk about categories we're interested in. And again,

• 19:51Speaker 02

  it's probably stupid because a lot of time goes into just like getting to know people, truly with no agenda on the table. And I'm sure at some point over the next decade, out of that, like a great entrepreneur will surface and it'll be someone that I got to know and I, and have had a longer relationship with. You know, I think in this world where an entrepreneur pops up and they're getting a deal done in seven seconds and you've never met them. Yeah, those are the ones where so much of this is you're betting on a single human's ability to be superhuman, super resilient, their ability to overcome every obstacle. And my partner Lucy has this great quote and I love it and I'm going to repeat it. "The things that you think will be easy will be hard. And the things that you think will be hard will be exceptionally hard." And we're like, and so we're like, everything about building a company

• 20:36Speaker 02

  is hard. There are very, very rare things that are easy. And so, yes, we really do, we like to get to know the founders early because so much of it is the founder, as we all know.

• 20:46Harry Stebbings?

  Totally with you. And I am very much with you also in terms of really getting to help them, often in the idea stage. I do want to touch on a different element that you said there. And you said about kind of differentiator and capital not being a differentiator anymore. And I spoke to our mutual friend Rebecca at USV before the show. And she said, you know, you've got to speak to Alexa about how she thinks about personal brand. How do you think about personal brand today in quite a marketing-driven VC world that we have today?

• 21:08Speaker 02

  First of all, I think probably personal brand exists everywhere. And I think as we all have these abilities to have our personal brand out there and build them in pretty much every platform that exists is a micro way to build your own personal brand. I almost think of it more as just reputation. None of us are perfect in my own career. I think I've learned lots and lots of lessons, but I really do believe reputation is everything. And you build your reputation one day at a time, one decision at a time. And in the same way that I think, what I really do believe LPs and our investors buy is our judgment. And they buy it every day, our full judgment, going to work, making one hour at a time, our best decisions that we can. And I really do believe in the inverse for an entrepreneur.

• 21:52Speaker 02

  What you buy is someone's track record of their trustworthiness, of their reputation, of their following through and showing up. And I think that's honestly, like, forget the rest of it. It's noise. It really is. Underneath it all, are you an incredibly good human who's going to make the best decision, who in the face of major adversity, because that will happen in all of our careers, and I'm sure I will face major dark days and hard decisions that I have to make, are you going to be fair and trustworthy? And are you going to take the high road? That's what I care about. And I care about that even beyond like my job. I care about it for my kids. Like, I want them to be like, my mom is a good human who every day makes great decisions.

• 22:29Harry Stebbings?

  I absolutely love that. And I couldn't agree more in terms of the reputation. My question for you on the reputation element is, generally, I hope mine's good. When mine takes a hit bluntly is I'm really bad at saying no. So either don't, terrible, I know, and that's like really an area for improvement, or I don't give a very specific reason, because I find then people just argue back with the reason and it's not productive. You're an entrepreneur, turned investor. You have that mindset, as we said, innately within you. What's the right way? And how would you advise me on the right way to say no?

• 22:58Speaker 02

  Yeah, so I will just share that I fully get it, Harry. And having had lots of people say no to me, and actually just like intimately knowing how much that that would hurt. That part of my, I'm a very empathetic person, as you probably can even just tell from this interview. Yeah, it sucks. And what I have learned is that the nicest thing you can do to somebody is say no early, say no honestly, and with real, real care. And sometimes I only know the way that I know how to do it, which is to say, I hate having to say no to you because I like you so much, but this isn't a good fit. And here are the three ways that I think I can help you otherwise. And it takes more time. And so I think, again, so much of our process is we only get closer to companies where there's a true and genuine chance of saying yes. Even then, you still have to say no

• 23:43Speaker 02

  lots and lots of times, more often than not, that all the odds are towards saying no. And in fact, this is a job of saying no. So just developing a real muscle. And anyways, I always recommend to people, you got to figure out your authentic way to do it so that you can do it yourself. And, Harry, you're never going to hate it less, ever. You just have to get good at it, because it is the part of the job. It is a core part of the job.

• 24:04Harry Stebbings?

  Yeah, thanks for that. That's really rich.

• 24:06Speaker 02

  Yes, sorry. I wish I could make it go away for you. I can't. You gotta get good at it. Do have a sentence which is L I T T P lean into the pain. We all know the things that we suck at, like lean in. You gotta get good at it. Just L I T T P lean into the pain. Develop your muscle at saying no, you gotta do it fast.

• 24:23Harry Stebbings?

  Well, I mean, speaking of leaning into the pain, one other way to do it is also really approach the advice element from mentors. And we did chat before about mentors and you said about the importance of having mentors of all ages. Now, I love this because I'm a strong believer in the mentorship model. But what do you mean by the mentors of all ages and why do you believe so strongly in this structure of support?

• 24:42Speaker 02

  So a few things. As I was 21, developing my career now over a decade ago, I didn't know much, right? I grew up in Jacksonville, Florida. My family's in medicine, so doctors, nurses, et cetera. I'm like the total black sheep in the business world. And I quickly learned that I don't need to know everything. I shouldn't expect to know everything. And that I should constantly surround myself with people that will broaden my perspective, add to the contours of my own thinking. And so the way that I just approached this was over time, and I almost just, the word mentor, I think of it as just friendships, like real genuine friendships. So I had a great guy named Anson Beard, who was the chairman of Morgan Stanley Securities when I worked at Morgan Stanley, who became my friend and he taught me two key things.

• 25:27Speaker 02

  Pick up the phone and call people when there's a, when there's something that you know should not be an email or a text. Pick up the phone and use your actual voice. You'll always respect yourself more for doing it. And the other thing is he was like, show up on time, like just be on time. And those two things have stuck with me for a really long time. Some of my old investors were incredible people of different decades, different generations, so in their sixties. And they talked to me a lot about how do I develop the ability to lean in a billion percent on my career? But I also, I have a family and I have three little kids and they taught me a lot of like, and, and I asked pretty graciously questions like rewind, what would you do better? What would you do better? And I kind of collected my own notebooks of these great pieces of wisdom.

• 26:08Speaker 02

  And then my final thing is like, I'm obsessed with 15 year olds and spending time with young kids and I'm, I, and I. And like, what do you guys think about, I actually asked a group of them, how do you think about your wallet? How do you think about money? How do you think about the world? What do you think about global warming? I mean, it was amazing. They were talking about, I was about to have a child and they were like, what's the cisgender of your child? And I remember being like, oh my goodness, they're just so much more open minded. And I loved it. It gave me a lot of hope for the future. But so I think just the way I think about, and even in the fun today, I mean, I can't list for you the number of people that maybe somebody else would say is my competitor, like a Josh Kushner who runs Thrive. You know, I've gone to him and said, hey, Josh, teach me. Or Sameer Gandhi and Archer Patterson, who founded Excel and were part of the Learn Best story. I said to him, tell me the things I'm going to get wrong.

• 26:53Speaker 02

  Give it to me every lesson. Or the guys at Slow or Pete Plin from NFX, who's a dear friend. And I said to him, Pete, I want the, the long list of every mistake I'm going to make. And I just approached this as I am imperfect. I know I'm not going to be perfect. And I would rather know where all the potholes are going to be as clear as I can. And I will still step in one, but that's kind of how I approach mentorship and friendship.

• 27:14Harry Stebbings?

  I totally love that. And again, we, I think we have such similar mutual friends. I absolutely love everyone you mentioned. So that was awesome. Pete Flynn, especially, very special man. Can I ask you a weird one? And it's, can your partner be your mentor as well? Or is that like?

• 27:27Speaker 02

  A hundred percent, a hundred percent. So actually it's really funny, but I'll, I'll tell you two quick stories. So Penny Pritzker, I met her, um, who's my business partner. I met her when she was in the White House as Secretary of Commerce. Her and President Obama tapped 10 entrepreneurs to be ambassadors for the country on entrepreneurship. I was a kid, like literally, Harry, I had no success. I was a complete kid. I was a puppy and they picked 10 of us and I was the baby and I was so nervous. I remember being like, oh my God, I'm literally going to meet President Obama in the Oval Office on entrepreneurship. Learn Best is so early. And Penny and I became friends and we actually ended up as part of the ambassadorship. It was a totally made up thing. It was pretty cool that they did it. It was totally made up. We had to travel with the White House and like share just the passion of how entrepreneurs build innovation.

• 28:11Speaker 02

  Because actually what's behind that is you build jobs and I really believe in jobs. Anyways, Penny and I really got to know each other and we chat a lot in common from our family dynamics. You know, I had lost a parent when I was younger to we both have brothers. And she sat with my mom and I in Morocco and we really got to know one another and we became friends. And she was somebody I looked up to. I admired deeply her judgment, her integrity, how she makes decisions. And when I was going to think about launching Inspired Capital, I really made, and Mark Batien and I had been sitting there, and I made two phone calls. One was to Penny Pritzker and I said, hey Penny, I think the East Coast could use an A plus fund that really thinks differently and is passionate about innovation and fueling the next thirty years.

• 28:55Speaker 02

  And we got off the phone. She said, you have to do that, Alexa. Absolutely. It's the right idea. And then right after we got off the phone, she shot me an email and said, you gotta call me back. And literally, she was like, wild idea. And I called her back and she was like, I want to be your business partner. I want to found this with you. Let's go. Let's bring a multi-generational stage to this. Let's think differently. And my second phone call wasn't even a phone call. It was to Lucy, who's one of my absolute best friends. She's a brain I admire deeply. She is a partner of mine. She's a best friend of mine. She's the godmother of my child. I'm the godmother of her child. And I was like, Lucy, we were the kids in this ecosystem. I think that the world would be better to have investors that bring our investing acumen, which is where we started, and also just our absolute love for innovation.

• 29:38Speaker 02

  And most importantly, our love of problem solving early, which again, building a company is just all day long problem solving. That's it. And the next thing we knew, it was, it was obvious we would always start something together. And then it was really funny because one day she was sitting next to me with her laptop open and I was like, we're doing this. And she was like, we're doing this. And it was so natural and so effortless. And so my partners are my mentors and are my friends. And again, that's kind of how we think about the world.

• 30:04Harry Stebbings?

  I absolutely love that as a founding story. That's a special one. I do want to ask one final question before we move into the quickfire. And it's actually about New York because I've spent a fair amount of time there and it seems super crowded when you look at it from the offset. But actually, when you get there, there's not that many funds that will like lean in and really lead around. There's a lot of people that will write follower checks, but I didn't see that many, and I'm saying five to ten plus, that will really fill in each stage. And is that right? And why?

• 30:30Speaker 02

  That's exactly right. I mean, I think that the way that, and this for me is. Probably as somebody just is, I love New York. I love everything about New York. The grit of New York, the resilience of New York, the diversity of New York, the thinking, the industries of which there are 10 that thrive here. First of all, New York can support so much more innovation. And as I said, every year, this ecosystem is growing and it really, there's $1 here to 12 in the valley. That's the math per capita. And so if you think about it, one, I love to think of New York City as the underdog, because in so many ways, it's the capital of the planet. And it's a really special place. And I love to think of it as an innovation underdog, because every day, I believe you see more and more people just getting sucked into this ecosystem.

• 31:15Speaker 02

  You have senior talent leaving the Bay Area wanting to come to New York City. And we're here to say, this is like a playground intellectually for us. We've been the kids of it. It's so collaborative. And everybody really is so friendly and wants to support it. And then we're here to leave big checks. We're here to write a main check into it, take a board seat when the entrepreneur wants that and help people navigate it. And so I'm obviously incredibly bullish on just the ecosystem of the East Coast over the next 30 years. And I think that it's just exciting every day to see the infrastructure that's being built around New York, from the banks becoming engineering shops to the Amazons and the Facebooks and the headquarters that are getting set up here. But also just to the intellectual, the academic ecosystem that's leaning in here.

• 31:59Speaker 02

  It's just a vibrant place. And for me, I wouldn't want to do anything else with my time.

• 32:03Harry Stebbings?

  That's amazing. I didn't know about the 12 to 1 ratio. That's a pretty astonishing and I'd be pretty happy being East Coast based if I were you then with that in mind. I would love to move into my favorite, though, the quick fire round. So you know how this goes. I say a short statement and then you hear me with your immediate thoughts. 60 seconds per one. Are you ready to dive in?

• 32:20Speaker 02

  Let's do it.

• 32:20Harry Stebbings?

  My number one New Year's resolution was to read more. What's the favorite book and why?

• 32:25Speaker 02

  So I think one of the books I really love is called The Power of Moments. And it's really about product development, which is we often try to make every part of the product development of a customer experience awesome. You just need one A plus plus plus moment. That is then how the psychology works so that you end up having a great experience. And so I'm always looking when I'm testing new products for like that one moment where you're like, wow. So Power of Moments is the book.

• 32:49Harry Stebbings?

  Who is the best board member you sat on a board with and what made them so special?

• 32:53Speaker 02

  So actually, it's this guy that is relatively unknown. His name is Lee Barber and he's in his sixties now. He was my board member. He had just sold his business to TD Ameritrade for about a billion dollars. And he is who I hope to be for every board that I sit on, which was he always gave me the toughest advice. And it really was like he cared so much. Every board meeting he came to, he was triple prepared, read everything, brought volumes of insights. And then always told me the thing that I did not want to hear because often sadly, he was right. He would say, this is going to be a big issue. This is a problem. These two people aren't working well together and one of them has to go. And he always did it with such empathy that he would send me emails at three o'clock in the morning being like,

• 33:36Speaker 02

  I know you're not sleeping, you're not in this alone. And I think because he had been an incredible CEO himself, like he understood how vital it was for him to push me harder and faster because we were never going to win if that didn't happen. But then on the flip side, he understood the humanity of I was just human and I was young and I was learning and I was going to make mistakes. And so he did it with such kindness and I want to die, you know, part of one of the reasons why I love Inspired so much is like, we want to do just that for every one of the companies that we get the privilege of being behind.

• 34:04Harry Stebbings?

  Tell me, what's the single biggest challenge of your role stay with Inspired?

• 34:08Speaker 02

  I mean, I think we already covered it. Say no, right? When, when you've had people say no to you and I've been on the other side of that and I know I would come home and be blue and my husband would be like, I'm so sorry, it's okay. In the early days, it would like really gut punch me and I would feel like I wanted to throw up and like I know what that feels like. And so as I said, I try to say no in a way where it's quick, it's sincere. And then I actually do something to help the entrepreneur get ahead.

• 34:32Harry Stebbings?

  What would you most like to change about in the world of venture and tech today? One thing.

• 34:37Speaker 02

  You know, right now it's so coastal, right? It's really, it's in it for a variety of reasons, ecosystems, maturity of the ecosystems. But I really do want innovation to spread. You know, my business partner Penny is a huge leader in Chicago and you're seeing pockets of innovation happening everywhere from Atlanta to Austin to Boulder and just making sure that over time, like we all pay it forward to all of those other ecosystems that are developing.

• 35:03Harry Stebbings?

  I totally agree with you there. Love a bit of Boulder. Final one that I have to ask, most recent publicly announced investment and why did you say yes and get so excited?

• 35:10Speaker 02

  So we just announced this, we were part of the Snack Pass round and two reasons. The two entrepreneurs there, Kevin and Jamie, were incredibly special. They have a bit of a contrarian view and I can't share their whole plan going forward just yet, but they have a bit of a contrarian view around food and they're just really special entrepreneurs and we loved the product and it literally has taken over campuses around the country and is growing rapidly and it was just a really, really fun one to say yes to and we just really love those two founders.

• 35:40Harry Stebbings?

  And as I said, I saw all the news when Inspired came out and I really wanted to make this show happen for quite a few months now. So thank you so much for joining me and this has been so much fun.

• 35:48Speaker 02

  Thank you so much, Harry, and thank you for everything you're doing for all of us. We're so grateful.

• 35:54Harry Stebbings?

  Absolutely loved seeing that one and the kind words there at the end really mean a lot to me and I can't wait to see the coming years for both Alaxa and Inspired. An incredible portfolio to be built, but I do want to say if you'd like to see more from us behind the scenes, then do check us out on Instagram. You can do that at H Stebbings 1996 with two Bs. But before we leave you today, this episode is brought to you by Silicon Valley Bank. For over 35 years, Silicon Valley Bank has been the bank for visionaries of all kinds, people and businesses who've revolutionized everything from software to social media, from workspaces to wine. With nimble banking services and solutions, Silicon Valley Bank helps startups adapt to the changing needs of a growing company. Learn more at svb.com backslash next. That's Silicon Valley Bank, ideas bank here.

• 36:37Harry Stebbings?

  Let's face it though, also, everyone not only needs banking, but everyone today wants to start a podcast, but man. The incumbent toolset sucks for creating podcasts, take my word for it. And that's why I love Descript so much. Descript is the brand new way to record, edit and mix spoken word audio. But for me, the main reason I just love it is because it takes your audio and it turns it into text. And so you can actually edit the text almost as if it's a word document and remove the audio and the text that you don't want. And it's super simple and just the best tool that I've seen for editing by far. We love it here. And now with our team at 20VC also, Descript has this amazing live collaboration feature. So we can work on the edits in real time. So we can comment, people can agree, disagree. Honestly, if you want to master your new podcast, you have to use Descript for the process.

• 37:22Harry Stebbings?

  And you can find out more at descript.com. They really have built something special, that's descript.com. And finally, as a VC, our job is to find the very best companies before anyone else does. And as an operator, you have to know who your competition is and how they're doing. And that's where Spectre comes in. Spectre formerly called CrunchDex. Essentially, do you want to know what is the fastest growing company in your city or vertical? Well, Spectre tracks 140 variables and growth signals from close to 17 million private companies worldwide and is a trusted partner to three out of the top 10 VCs. To learn more, check out trispector.com, that's trispector.com. As always, I so appreciate all your support and it really does mean a lot to me.