Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: Biggest Lessons From Opendoor's Scaling Journey, How To Implement Systems for Growth & The Right Way To Structure Customer Discovery Processes with Julia DeWahl, Angel Investor About this episode Julia DeWahl is one of the rising stars of the Silicon Valley angel investor community with a portfolio including the likes of Linear (Sequoia-backed), Modern Fertility (USV backed) and Primer (Founders Fund backed). Prior to angel investing Julia was one of the first 10 employees at Opendoor seeing their hyper-growth first hand in many different roles from Head of Seller Experience to being General Manager of Pheonix & City Operations. Before Opendoor, Julia spent 3 years as a consultant at Bain. If that was not enough, Julia is also an avid cyclist and is setting up a women's cycling apparel line alongside her investing. In Today’s Episode You Will Learn: 1.) How Julia made her way into the world of startups with Opendoor from Bain and how that position at Opendoor led to her angel investing? What were the 1-2 takeaways for Julia from her time at Opendoor that have most impacted how she angel invests today? 2.) Customer Discovery: When is the right time to engage in deep customer discovery work? How does one select the customers to go deep with? How does Julia structure the process? What questions are most revealing? Where do many go wrong? How does one determine the feedback to accept vs which to reject? 3.) How does Julia think about implementing systems for growth? What is the structure of these systems? Where does one start? How does Julia determine the metrics to track and focus on? How does Julia balance between growth vs profitability? 4.) Does Julia believe people can really scale with the company? What are the leading indicators that people are struggling to scale with the company? How does Julia advise generalists to survive and thrive in a scaling organisation? Should they specialise? 5.) What have been some of Julia biggest lessons of what it takes to be successful as an angel today? Who has Julia learned and gained the most from in this new discipline? How does Julia measure her own success as an angel? What are the core challenges? Items Mentioned In Today’s Show: Julia’s Fave Book: The Courage To Be Disliked: How to free yourself, change your life and achieve real happiness Julia’s Most Recent Investment: Primer: Homeschool with superpowers As always you can follow Harry and The Twenty Minute VC on Twitter here!
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? This is the 20 minute VC and I'm so excited for the episode today. I've heard so many good things, both from founders and VC friends of mine about this guest. A phenomenal operator now turned angel investor and one that I've actually co-invested with. And so with that, I'm very excited to welcome Julia DeWahl to the hot seat today. Now, Julia is one of the rising stars of the Silicon Valley angel investor community with a portfolio, including the likes of Linear, Sequoia backed, Modern Fertility backed by USV and Primer backed by Founders Fund. Prior to angel investing, Julia was one of the first 10 employees at Open Door, seeing their hypergrowth firsthand in many different roles from head of seller experience to being general manager of Phoenix and City Operations. Before Open Door, Julia spent three years as a consultant at Bain. And if that wasn't enough, Julia is also an avid cyclist
0:43 Harry Stebbings? and is now setting up a women's cycling apparel line alongside her investing. I absolutely love that. And I do also want to say a huge thank you to Mike Vernell at Sequoia and JD Ross at Atomic for the fantastic question suggestions today. I really do so appreciate that. 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 Carter.com/20vc 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 in real time data in the Carter platform and work with Carter's team of experienced fund accountants.
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3:00 Speaker 01 You have now arrived at your destination.
3:03 Harry Stebbings? Julia, it is such a joy to have you on the show today. I've heard so many great things, both from Mike Vernal at Sequoia and then also JD from Atomic. So thank you so much for joining me today first.
3:12 Speaker 02 Great, thanks for having me here. It's great to be here.
3:14 Harry Stebbings? Not at all. I'm excited for this one, but I do want to start today with a little bit on you. So tell me, how did you make your way into the world of startups and tech? But most importantly in that, what I'm most interested by is how did you come to be the prominent angel that you are today in the valley?
3:26 Speaker 02 I moved out to the Bay Area in 2013. I knew I'd wanted to get involved in tech in some way. I'd seen a lot of the most ambitious people I knew moving to San Francisco to start or join startups. And it just felt like this was where the action was. And I continue to think that that's true. I first heard about Open Door through a TechCrunch piece in the summer of 2014 and was really compelled by the idea. And I joined the team there as the 10th employee in an ops role, which at the time just meant everything non-technical. And while I was at Open Door, I built and led our customer operations team. I was the GM of our first market, Phoenix, as well as the broader city ops team as we expanded. And then was chief of staff to our CEO for a year. And that was really my first experience at a startup, was there for around four and a half years.
4:10 Speaker 02 But while I was at Open Door, I started to get some exposure to angel investing. And Eric Wu, Open Door's CEO, was actually a big part of that. So he shared a bunch of decks on He was looking at, he introduced me to other angels. And then my good friend, Afton Vetri, started Modern Fertility. And that became my first investment. Soon after that, I joined Sequoia's scout program and started writing some more checks. And I absolutely love it, and I don't think I'll ever stop angel investing.
4:35 Harry Stebbings? I mean, it's also a rather wonderful one. Afton is the first check. I had her on the show and she was an amazing guest and what an incredible company. So I'm excited to hear about that. I'm really interested because it's such an incredible experience seeing the hypergrowth at a company like Open Door. And so if you were to think back to the time, and now especially, if you were to choose one to two takeaways from your time with Open Door that impacted, I guess, both your operating and investment mindset, what would those one to two takeaways be, do you think?
4:59 Speaker 02 Absolutely. There were so many things I learned at Open Door. But one that stands out and that I find myself thinking about frequently as an investor is people solve problems with the tools that they have. That means that a founding team and their first hires there need to be matched to the core competencies required for that business. So take Open Door, for example. Those core competencies that we needed to be really good at were pricing, it was operations, it was capital market. With pricing, Open Door's co-founder Ian is a data scientist. And so he was responsible for pricing accuracy and he had that depth of experience in the field. He had a network there and it was really critical to get right. We had to make sure Open Door was delivering on fair offers so that we weren't coming in too low and hurting our reputation.
5:44 Speaker 02 People would call us lowballers or coming in too high, which meant that we would buy a house that then we'd take a loss on when reselling it. So really critical that he was a part of that founding team and that he brought that focus to that part of the business that he worked on. He continues to work on to this day. And that really impacted my lens on investing, which is the founder market fit question is really important to me. So when I meet a founder, I always ask myself, is this the right person to start this business? What are the core competencies required to be successful? And do they have those skills and attributes to do those things?
6:16 Harry Stebbings? I love that in terms of the founder market, but can I ask you, because you said there about kind of building that data model from the early days. I've heard Keith Roy say he loves businesses where the whole vertical stack is owned end to end by the kind of company and the provider, and they're not reliant or dependent on anyone else. Do you share that when you're looking at investments today? Or are you a little bit more flexible in terms of being willing to be more reliant on platforms, on ancillary products and services, rather than owning the whole vertical solution?
6:41 Speaker 02 Oh, I'm a big believer in owning the vertical solution, the end to end customer experience, because ultimately you have control that way. And they're absolutely harder businesses to build, right? You have to work on a whole bunch of components at once to stand something up. So take Open Door, you had to build out how to price something, how to price a house sight unseen. You had to build out an entire stack of customer operations. And that included everything from actually talking about and selling the product, but then also actually buying and selling houses and maintaining them, renovating them, getting signage up in the front yard. But if you didn't own those little pieces, you risk having a disjointed experience when buying and selling a house. And that's actually what happens today, right?
7:22 Speaker 02 The current experience is really fragmented, you're working with multiple parties. Whereas when you go to Open Door, you're just working with one person, with one company, and you're getting this really like smooth holistic experience, which I think makes Open Door stand out against its competitors. So definitely a big believer in the vertically integrated business.
7:40 Harry Stebbings? I am also interested to ask with the Open Door experience in mind, you know, a lot of graduates coming out of college saying, they always ask me kind of one of three options, and I'm always slightly nervous about what to advise them with the kind of weight of responsibility. So I'm going to delegate this to you on this one. So they always say, should I join a startup? Should I start a startup? Or should I join an incumbent? How would you advise them, given your first hand experience with Open Door? And then also, funnily, investing in the next gen of the newest startups rising today?
8:05 Speaker 02 Yeah, it's a great question. I would encourage everyone to begin with considering the start a startup path. I think it's like, why not? Most people, I think today, don't think or dream big enough. And just going through the process would allow them to think about, okay, what might I work on? What might it take to start something? And I think that's really valuable thinking just in and of itself. That said, each of the paths has something different to offer. I think joining a larger company, you hopefully get exposed to best practices of a larger organization. You probably work for someone more experienced than you, more specialized potentially. Going to a startup, you're probably going to end up taking on a role that you kind of wouldn't have gotten elsewhere otherwise. And so each of those paths has its pros and cons. I'd say that just whatever path you choose, the most important thing is to make sure you feel
8:50 Speaker 02 like you're working on the edge of your abilities and you're achieving the kind of growth that you want for yourself every day.
8:55 Harry Stebbings? Yeah, as a pre-seed and seed investor, I would definitely say start a startup, but mine might be slightly biased. But I do want to start, we mentioned kind of owning the entire kind of customer lifecycle there with kind of the vertical discussion. And I'm interested because I want to start on really the beginning of the lifecycle of a customer and customer development is always core in that element. So when is the right time to really engage deeply in this customer development process, do you think? And then secondly, how do you select the customers you engage with?
9:21 Speaker 02 Yeah, absolutely. I think the best time to start is at the beginning, right? I'm a huge advocate for talking to customers as much as you can. And I've found that over time, you really can discover that next level of nuance and insight that you actually probably don't need to get to that first kernel of an idea, right? But later on, you sort of hone it, you learn more, you discover who your power users might be. I really like the term that Mike Maples uses, value hacking. He talks about just like really digging in there and understanding like, is this something really valuable? Who loves this thing? And then I do think it is important to kind of pull up, look around at the landscape. Are there other customers like this who are going to become power users? Or am I risking building something that's a bit too niche?
10:05 Harry Stebbings? Totally get you in terms of kind of discovering those power users. I guess when you reflect on your process, what does it look like? How do you structure it? And are there core questions that you found most revealing in terms of discovering what customers fundamentally want?
10:17 Speaker 02 Absolutely. I think I always advise that people start with broad, open-ended questions. You really can't go wrong there. This allows the customer to actually more proactively bring up areas of concern or frustration that they have, just to share what matters to them. And if you start with a set of more specific questions, you actually risk kind of steering that customer down a certain path and they might not have actually brought something up that is really valuable and you would have wanted to know about. For example, when we were focused on building the seller product in the beginning at Open Door, we were again so focused on building a product that was all about selling. But when we went and started Asking people to tell us about their experience selling their home, they were often talking to us about their next dream home,
10:59 Speaker 02 that they were so excited about buying and how they needed to sell their current home to be able to afford the down payment for the next one. And they just wanted to remove the stress and hassle of the sale and just be done with the whole selling part. And that really transformed the way we saw ourselves and we saw the open door product. Selling was often in combination with buying. And so that came through in our product marketing. And I think ultimately helped us develop a more compelling pitch to our customers.
11:23 Harry Stebbings? I'm really interested, you said there about product marketing. How should teams use this data that you gather in this kind of incredible customer discovery process? In the development in terms of the product marketing aspect?
11:32 Speaker 02 Yeah, one of my favorite questions to ask customers is, how would you describe Open Door to a friend? I find that this allows you to really understand how someone else would describe the value proposition or the positioning of your company better than a Realtor for X, Y, Z reasons, those sorts of things. They really end up emphasizing what's important. I always find it's best to use a customer's own words in marketing that's going back out to those same customers.
11:58 Harry Stebbings? Totally agree, especially kind of that verbiage that they use. I guess my concern always with customer discovery, especially when it feeds back so intensely into product and product marketing is, how do you determine between the feedback and the data to accept and ingest and really kind of work with versus which to reject? And I guess going back to Thomas Ford, like how not to build the faster horse?
12:17 Speaker 02 The customer is not meant to be the one coming up with a vision for your product. So they're there to share their feelings, share their concerns, share their frustrations. And then it's the responsibility of the product builders to synthesize what they've heard and be the one visioning the future, right? Looking around and saying, what can we build that's better here than crafting that elegant solution? So I would say, don't ask, hey, what feature do you want? Because the customer may not know. They also may not be thinking in that big way that I think here in Silicon Valley, we're taught to think. So I would say definitely that's a responsibility of the product builder.
12:52 Harry Stebbings? Yeah, absolutely. No, I do agree. If we take that kind of one logical step further, then we can move more to the company scaling perspective. Because if you get it right, hopefully magical product market fit ensues. And I guess when you look back at the scaling journey for you with Open Door, you said before about the importance of building systems for growth and moving metrics. Can I ask, what did you mean by this, building systems for growth and moving metrics?
13:13 Speaker 02 Absolutely. Building systems is really important to allow other people to come into the company and start operating, to figure out how to enable technology to actually make you more efficient at what you're doing. It really just means putting those rules and process in place around the things that are happening repeatedly in the business. In practice, what that means, kind of to get started doing that, is writing everything down or drawing out the flow charts of kind of everything that's going on in the operation. So first this happens, then this, who's involved, what are the dependencies, what data is required or what data is generated. At Open Door, we started building our first systems out in spreadsheets. We use Asana templates at one point, email workflows, Slackbot, Zapier, you name it.
13:55 Speaker 02 I think it's super important to iterate for a while in the most lightweight tools that you can get away with, because inevitably you're going to be changing the way you do things. A mistake we made a few times early on was to commit to code some processes that just weren't fully baked yet and were continuing to evolve. And then because engineering resources are limited, which they often are, we had to keep using these outdated systems that we had prematurely built for longer than we would have liked.
14:21 Harry Stebbings? How long is long enough data to know that a process is right versus need to be iterated on? Is it like a couple of weeks? Is it a couple of months? How do you think about knowing when a process is right to be coded?
14:31 Speaker 02 It depends on how complex your operations are. I think it depends on the pace of the growth of the business. Somewhere between a few weeks and a few months is probably around, right? When you do something for a week and think it's working, like you probably just haven't hit the edge cases yet. So give it a little bit of time. And then again, inevitably, engineering resources are going to be limited. So you will find yourself naturally wanting to prioritize the areas that you do think are kind of the most locked. And so start there, let yourself kind of scrape by with spreadsheets for a while on the other stuff. But it can be almost Worst to put something into code that you know kind of won't get prioritized or revisited for a while and then have to be working on something that's a little bit stale and outdated.
15:10 Harry Stebbings? I mean, these processes are kind of obviously generate actions and metrics. And I'm interested on the moving metrics out of it because we often hear about kind of the hailed north star that's unwavering. What are your thoughts on moving metrics and how do you approach that?
15:22 Speaker 02 Yeah, it's a great one. Moving metrics usually means they're stuck, right? If you're saying, hey, this metric isn't going anywhere. What's going on? How do we move it? The cost, for example, was a great one at Open Door. We always wanted to remove costs. We wanted to work on our margin. One of the things that we focused on at Open Door was what are the root causes of why maybe this metric isn't moving? And so some of the engineers at Open Door actually introduced me to the framework of asking the five whys. You just ask why over and over again. And a lot of this digging deep into what might the root cause be, I think, was helpful in then coming up with new ideas, generating new thoughts around how you could kind of break through and come up with new ways to fix things.
16:02 Harry Stebbings? Yeah, no, absolutely. I mean, I guess when you have these metrics and they're a little bit more baked out with the priorities and processes, you have to communicate them across the company and the teams. What have you learned and seen about the best way to truly communicate the priorities throughout the org and what works?
16:17 Speaker 02 Yeah, I would say keep it simple, make it memorable and explain the why. There was a point where we were working on hitting unit profitability in our core cities where Eric decided he would show up to work every day wearing this blue T-shirt with the single most important company metric on it. And so everyone at the company knew the goal. I'm definitely not saying T-shirts are the only answer here, but keeping it simple was really key. I will say the danger to using just a single metric, though, is what might be sacrificed to get there. So at Open Door, for example, if we raised our offers on people's homes, we'd see a bump in conversion. So yes, we would therefore hit our growth goals, but profitability would have suffered.
16:55 Speaker 02 Paired metrics are a great way to try to mitigate some of this. So saying, okay, this is our top line goal, but this other metric can't go below X.
17:03 Harry Stebbings? Yeah, no, absolutely. It's that awkward balance, but I totally agree in terms of favoring the paired metrics. And this episode was brought to you by Tshirts.com, who are our kind sponsor. I do want to ask, I heard from, I think it was Mike Vernal, actually, that you also have themed for checklist as part of the scaling process. So it taught me how do you use checklist so efficiently? And I'm honestly, I'm terrible with checklist. How do you advise me and others to do the same?
17:26 Speaker 02 I am not a perfectionist or overly detail-oriented person, so this is absolutely a hack. Atugwande wrote this book called The Checklist Manifesto with the subtitle, How to Get Things Right, and that's exactly what they're for. So checklists are really about delivering consistent quality. And if you think about what the mandate of the operations team was at Open Door, it was exactly that. Another thing I'll say about checklists is that the person doing the checking should be responsible for the creation and the ownership of the checklist. Nobody wants a checklist if it's not actually useful. This is not one of those things where the manager writes it and hands it down to the team. In fact, I think it would probably have a bad outcome because the team actually knows the details of what's going on in the field or on the phone with customers.
18:09 Speaker 02 And instead, having the team create and edit and manage their own checklist over time worked really well.
18:15 Harry Stebbings? I have a big question for you here, and it's, can you assign two people to a single task on a checklist? And what are your thoughts on kind of how that accountability drops, or does it not, if two people or more are accountable?
18:26 Speaker 02 Absolutely not. You need to have one person accountable. This is really important for something like selling and buying a house with Open Door, where there really were a lot of steps and there were different people involved. We built an admin system within Open Door where each of the things on the checklist was assigned to a role at the company. So it might be the customer experience person or the field ops manager. And then next to that, within that role, there would always be a specific name. And that was really critical for making sure people knew exactly what they were responsible for. And then if there was something that went wrong, we could figure out, hey, who was supposed to be doing that?
19:00 Harry Stebbings? In terms of the people there that we mentioned, obviously, people are central to all company growth, scaling, and really everything that we do. My question to you is, having seen the incredible growth of Open Door and having scaled with it, a lot of people have told me on the show that people are destined for certain stages of company development and growth, and maybe they're not flexible to scale. Do you think people truly can scale with scaling companies? And what are the indicators that they can scale with the company?
19:23 Speaker 02 I've seen some people scale remarkably well with the growth of fast-growing companies. And I think they all typically possess a really strong growth mindset. But that said, I don't think it's reasonable to expect that everyone would scale with a fast-growing startup. And for those who don't, it cannot always feel great to be layered, right? Get a new manager above you. But oftentimes, people really do end up learning a lot from that person who was hired to be their new manager. And typically, if that's happening, it means your company is probably growing and doing well. So all of that is very positive.
19:54 Harry Stebbings? Can I ask, what's the right way to layer? Because I have a lot of founders who say, I'm bringing in someone external and Julia or Suzanne is going to be upset about this. What's the right way to do it to not make her unhappy, disincentivize her? Do you have any thoughts or advice on the right way to layer?
20:09 Speaker 02 Yeah, I think it's important to actually bring the person in on the fact that you are going to be hiring someone in above them. Not necessarily to be interviewing them, but to kind of give them a bit of a heads up and to say, hey, this is what we're looking for. So here's our criteria. We want someone who has these skills or this many years of experience doing this thing. And they kind of understand the rationale and they're not blindsided by it. Because it kind of feels like they went behind your back or you weren't aware and you're surprised by it, and not in a good way. So that would be the one thing I would say. And then the other would be to also just communicate to the team more broadly that the company is doing well. You're excited that these really experienced people want to join the team, right? And that they have done X, Y, Z things at other places. And they're going to actually add a ton of value to the team.
20:53 Speaker 02 And that the bar for staying hungry, staying scrappy, being hardworking does not change. And that applies to everyone, including new, more senior executives joining the team.
21:02 Harry Stebbings? Yeah, absolutely. In terms of really exciting the team with the quality of people that you're bringing in. You spoke about kind of scaling people there. And as I said, you scaled exceptionally with an open door. And it was a question for me, which is like, generalists often have perspectives on scaling. And when we spoke beforehand, you mentioned thriving as a generalist. How do you think about thriving as a generalist? And how does one navigate that career path as a generalist, do you think? Especially with scale.
21:24 Speaker 02 Generalists tend to thrive in environments where there are a lot of nebulous problems to solve and kind of no overly specific skill set is needed, kind of need a lot of a few things. And this happens time and time again within fast growing startups. So generalists can be hugely valuable in those first few years. And they tend to thrive at the intersection of multiple disciplines, whether it's across quantitative and qualitative. And navigating a career here is, I almost think, easier in those first few years than it is later, because as organizations grow, you do need to have more specialists, you do need to have people with kind of more years of experience. So my advice here would be to first, raise your hand to just say, I'm here to work on whatever's critical, like put me to work and just bring that growth mindset, right? I can go ask a question if I'm not sure to
22:09 Speaker 02 do something, or I'm gonna go Google it and look it up and figure it out. And then the second thing I'll say is, don't be afraid to take on a specialist role. There were, myself included, people who went from general kind of biz ops and generalist operations to, I'm gonna go lead a sales team. And that means I'm gonna go learn a lot about sales, I'm going to do sales myself, I'm going to get mentorship from other sales leaders. And I think generalists do have that ability to learn quickly on the job. And so I would say, don't be afraid to lean into trying to take on a specialist role.
22:39 Harry Stebbings? In terms of evaluating people, I spoke to a mutual friend of ours, Mike Vannell at Sequoia before the show, and he said that he's always intimidated by maybe financially and operationally complex businesses like Open Door. And he asked, given the experience, how do you think about evaluating founders for these very complex businesses, often with kind of very real world components?
22:59 Speaker 02 For what it's worth, I'm also intimidated by financially and operationally complex businesses. I've seen it firsthand. There are a lot of things that need to go right. As for evaluating founders for these types of businesses, I look for systems thinkers who are detail oriented, but can also think strategically about the structure of their business model. So they're thinking about things like economies of scale over time, where they can deploy technology to reduce costs. They need to be fairly comfortable sifting through data and analyzing a P and L, because really what makes these types of businesses work happens at that detailed level.
23:33 Harry Stebbings? Can I ask, how is that uncovered? When you think about those systems thinkers, what kind of, do you know what I mean? Because you obviously can't ask, are you a systems thinker? What kind of questions reveal someone's mindset towards being more systems thinking than others?
23:46 Speaker 02 It's a great question. I think it's actually hard to do in sort of like a one hour coffee meeting. What I will look for are someone's ability to talk through the business structure. So how do they make money? What is their margin structure looking like? What are the costs associated with the business? How do those change over time? How do they think about deploying technology against any operational component they have in the business? And I do look for them to also acknowledge that, hey, we're going to use people here. And we're going to build a playbook and hire people to do this job. It kind of reminds me of Flexport or something. It's the people who are telling you they're going to automate everything they do. I also am quite skeptical. So those are the types of questions I'll ask.
24:25 Harry Stebbings? Yeah, absolutely. In terms of the questions you're asking, kind of the evaluation of those people and fitting for the business. Obviously now kind of angel investing a lot more. And with your name on, as we said with Modern Fertility, some of the best cap tables. Another mutual friend of ours, JD at Atomic, asked, you have a unique skill set in seeing people adapt to new roles. How are you self assessing yourself in this new world of angel investing?
24:46 Speaker 02 JD and I both had to adapt to a lot of new roles at Open Door over the years. And angel investing in some ways isn't too different from learning anything else for the first time. I've focused a lot on learning from others. So whether that's through blog posts or Twitter or a conversation with other investors. People have been so generous with their time, as I think they have been with you. It's a really special place to be here in Silicon Valley. Although it's funny, so many of them just happen on the internet too, that you're kind of like, well, I also could be in London. And it's really great that I think this community really values generosity and sort of bringing people along. As for my own self assessment, I think in some ways it's too early to tell, right? It takes at least five, if not 10 years to see a company exit.
25:28 Speaker 02 So talk to me in a decade and I will be able to give you a much better answer. But I think I have a few unicorns in there somewhere. And I think where I am strongest and best able to support founders is in thinking through customer development in kind of that zero to one product stage, in hiring and people related topics. Did a lot of that at Open Door and then in building out and scaling up operations.
25:49 Harry Stebbings? You said about kind of learning from those people. I'm very keen to kind of share the spotlight with those people who have been amazing to me. I mean, two for me are like Mike Maples and Brad Feld. Always been unwavering in terms of that support and kind of knowledge guidance for me. Who's been kind of instrumental in your adaptation of the new role and really just building the knowledge base?
26:07 Speaker 02 Well, there are some people who I've actually never met who have been influential on me. I think about Paul Graham and his essays. I think about the P. Marker archive that I've read. I haven't met either of those, although maybe at some point I will. And then there are people like Mike Maples, who has been generous. We've had a couple of Zoom calls. Love listening to him on podcasts. I think he has some amazing thinking. Mike Fernall has been amazing over at Sequoia. He always takes the time to respond to my emails where I'm kind of outlining, hey, you know, I met with this company here, so I'm thinking about it. He'll ask some great probing questions back. We always have a lot of good discussion. So he's been wonderful as well.
26:42 Harry Stebbings? Final one before we move into the quickfire. In terms of kind of actually how you think about investing, we chatted before and you said, be wary of vitamins. Talk to me, we've seen some incredible vitamin businesses being built, but why do you maybe feel more kinship towards the painkiller style of business and be wary of vitamins is prominent for you?
26:58 Speaker 02 I think of the vitamin painkiller metaphor as more of a spectrum than maybe a one or the other when it's applied to startups. It's really a rule of thumb to make sure you're being rigorous in evaluating whether a product is actually 10x better than whatever already exists out there. I've seen people develop products that I just feel like they're kind of forcing the narrative on it being better than the alternatives. And so I'm very wary of that. I also think that you can risk things like high CAC and low conversion and high churn. If you're not really clear upfront about the product being 10x better than the alternatives today. And I also finally find that vitamin type products are often the first to go in a downturn. So you want to be that must have product, not the nice to have.
27:40 Harry Stebbings? I mean, you've just said the word that I think about multiple, multiple times a day, which is CAC. And so I just have to ask it while I have the chance. And it's both of us invest pre-seed and seed. And bluntly, I always actually slightly diminish the importance of kind of analyzing CAC at seed because it's so transient, it changes so much, it's so platform dependent. And really, it's just such an unreliable metric in my eyes, especially at this early stage. How do you think about kind of the centrality of CAC and how much weight and prominence do you assign it?
28:08 Speaker 02 I think it's hard at the very early stage. You can try to look for benchmarks, right? But you won't really know what that cat cost is going to look like. I do look for people who have given it some thought. So they say, hey, we acknowledge we're going to use paid marketing here, but we also have a unique and creative strategy over here about how we want to generate word of mouth, how we want to generate referrals, how we want to use content, maybe try to lean into SEO. I don't think SEO is dead. So if someone is being sort of holistic about how they're thinking about that blended cat, I think that's really important. But at the very early stages, I think it's hard to know.
28:40 Harry Stebbings? Yeah, no, I'm glad that we're aligned there. I do want to move into my favorite, though, which is the quick fire. So I say a short statement, Julia, and then you give me your immediate thoughts in about 60 seconds. Are you ready to dive in?
28:50 Speaker 02 I'm ready.
28:51 Harry Stebbings? Because I'm dying to read more. Tell me, what should I be reading and why?
28:54 Speaker 02 The courage to be disliked is one of my favorite books. It is a philosophical book written by two Japanese authors that explore the work of the psychologist Alfred Adler. And this is one of those books where you just want to pick up a notebook while you read it. There's so many little nuggets of wisdom in it. And overall, the book just encourages people to really own their outlook and their mindset and to chart their own path from there. Would highly recommend.
29:16 Harry Stebbings? What's the biggest challenge of angel investing stage, you think?
29:19 Speaker 02 I think for most people, it's finding the time to get to know others, to be out there in the Twitter sphere or wherever it is where people are talking about ideas. I think finding the time to really get to know the problem space and the team, once they've engaged with someone. Because most angels aren't investing full time. They have day jobs they're focused on. And it can be hard to carve out time within a few days' notice to research a space and get to know founders.
29:41 Harry Stebbings? What more to our saying do you most frequently revert back to? And why?
29:44 Speaker 02 I love the saying by Maya Angelou, which is, "I've learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel." And I think this works for me both ways. I like to be intentional about being present with people, listening and how I might make others feel. And then it goes the other way, too. I try to listen to my gut more on people. How do they make me feel? Do I want more or less of them in my life? My favorite is when I feel more curious and optimistic when I'm with someone. And I say to myself, this is the type of person I want to be around more.
30:15 Harry Stebbings? If you can see my face now, it would be great because it's one of my favorites by far. And so I'm so pleased to hear that one. Tell me, operating a business and investing at the same time, how does it make you a better investor?
30:25 Speaker 02 Yeah, operating and investing are incredibly complementary. Investing encourages you to be up there at that 30,000 foot view, seeing patterns across industries, comparing business models, looking at macro trends to see where those next pockets of opportunity might be. But operating is much lower altitude. I would call it more bird's eye because you don't also want to be sort of like in the weeds for the whole time. But it allows you to sort of observe what's going on within your business to see, hey, over there, product isn't working out. And then I think those two things can be very complementary. Investors understand what it takes to operate something. And then on the flip side, operators are able to invest, thinking a bit more strategically, having looked at other businesses before, and then also understanding when to raise money.
31:08 Harry Stebbings? We both love cycling. What are the similarities between cycling and scaling businesses, do you think?
31:12 Speaker 02 It's hard. It's painful. You're going to experience pain along the way, but that's what gets you to the top faster than your competitor. This is what makes your muscles grow stronger over time. Both can benefit from that Hulk mentality that you get stronger with adversity.
31:27 Harry Stebbings? I was gonna say it's bloody long, but yeah, totally. I'm aligned with yours as well. But tell me, what moment in your life has served as an inflection point and maybe changed the way that you think?
31:36 Speaker 02 Joining Bain out of college was a big inflection point for me, actually. School had always come relatively easily, and Bain was the first time in my life where I struggled and I had to work really hard. Bain had this concept of zero defect. And for someone who's not particularly detail oriented, my job was just bootcamp every day. But ultimately, this paid off. I think, one, I have a much stronger work ethic and just overall stamina for working through hard things. Two, I realized the power of putting effort into something.
32:04 Harry Stebbings? Tell me, final one, most recent publicly announced investment, and why did you say yes and get so excited?
32:09 Speaker 02 My most recent publicly announced investment was in Primer, where I know you're also an angel. They're building full stack homeschooling software. This one was very team driven. Ryan and Maxim are both proven get things done leaders. They're quite complementary in their skill sets, and they're both really passionate about what they're building in the space. And I believe there is enormous opportunity for innovation there.
32:30 Harry Stebbings? Yeah, I could not be more excited for that. So I'm thrilled that that's our first together and to many more together. But thank you so much for joining me today, Julia, and I so enjoyed this one.
32:38 Speaker 02 Thanks so much, Harry.
32:41 Harry Stebbings? So fantastic to have Julia on the show there. And if you'd like to see more from Julia, you can find her on Twitter at Julia DeWol. Likewise, it'd be great to welcome you behind the scenes here. You can do so on Instagram at HStubbings1996 with two Bs. But 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 Carter.com/20vc 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 in real time data in the Carter platform and work with Carter's team of experienced fund accountants. Again, go to Carter.com/20vc to get 10% off.
33:25 Harry Stebbings? And speaking of amazing products that you've heard about with Carter there, last month I had Jeff Seibert and Wayne Chang on the show from Digits. Simply put, they're two of the best founders that I've ever met, and they're creating the most intuitive financial software that you've ever seen or used, automatically analysing your company's spend and visualising it for you as it happens. Hone in on recent activity, trends, anomalies, or any question that you have in just a few clicks. And unlike every other financial software, the integrations is not weeks, it's just a few clicks. I have to say, the product is absolutely beautiful, which is not something I ever thought I'd say for financial software, but you have to check it out and you can do so at digits.com. That's at digits.com. And finally, did you know there will be 1.4 million job openings for developers in 2020 alone?
34:09 Harry Stebbings? Well, that's when my friends at Terminal come in. Terminal is a remote teams engine for fast-growing companies, connecting you with global talent to deliver the product-building powerhouse your business needs to grow. They provide services and infrastructure in a complete solution that allows businesses to build and scale their remote engineering teams from the ground up without sacrificing experience or quality. From workspaces to community to on-the-ground support, they take the guesswork out of remote so that you can really thrive. But really, don't take my word for it, just ask high-growth businesses like Gusto, Chime, Earnin and Hims, all trusting Terminal with their remote teams. And you can find out more today at terminal.io. As always, I so appreciate all your support and I can't wait to bring you another fantastic set of episodes next week.
Previous 20VC: Oren Zeev on Why Diversification Is Overrated, The Downside of Thematic Investing, Making Quality Decisions In Uncertain Conditions & Why He Has No Reserves Allocation Next 20VC: 8VC’s Joe Lonsdale on How To Foster Contrarian Thinking Within Venture Partnerships, Why The Best VCs Are Company Builders & Why It Is Not Possible To Build Multi-Billion Dollar Companies and Have Worklife Balance Page updated October 26, 2026 · transcript and summary are machine-generated
