Minnie Ingersoll is the cofounder of Shift which is an online marketplace for buying and selling used cars. The compány has raised $300 million from investors such as Highland Capital Partners, Great Oaks Venture Capital, and DCM Ventures to name a few. She is now a partner at the early stage VC TenOneTen and also hosts the LA Venture podcast.

In this episode you will learn:

  • How to run a used car dealership out of your friends’ apartment in San Fran (and park 7 cars there at a time)
  • How Shift mastered the chicken and egg dilemma facing marketplace startups
  • The types of startups Minnie Ingersoll is funding now
  • What she most wants to tell new entrepreneurs
  • Her favorite interview questions for prospective product managers

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Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.

About Minnie Ingersoll:

Minnie Ingersoll is the host of the LA Venture podcast, and a partner at TenOneTen actively investing in great teams. They are operators who invest early (pre-seed, seed, seed+) and love working with technical founders who are passionate about what they’re building.
 
Prior to TenOneTen, Minnie Ingersoll was founder and COO at Shift, an online marketplace disrupting the $1.2T car industry by providing a better experience for buying and selling used cars. Grew to a $100M+ business and a recent Series D.
 
Minnie Ingersoll started her career as an early product manager at Google where she co-founded the Access team; a cross-functional product, policy, and engineering team that spun off Google Fiber.
 
In her spare time, Minnie Ingersoll volunteers for city government, surf baby waves, and raise baby people.
 
Connect with Minnie Ingersoll:

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FULL TRANSCRIPTION OF THE INTERVIEW:

Alejandro: Alrighty. Hello everyone, and welcome to the DealMakers show. I think that we’re going to learn quite a bit with our guest today because I think that she’s seen it all, done it all, been on very large rocket ships and has also done her own, and now she’s going to the other side of the table as an investor. So without further ado, let’s let her tell us about it. So, Minnie Ingersoll, welcome to the show.

Minnie Ingersoll: Thanks, Alejandro. Glad to be here.

Alejandro: Originally from the land where movies are created from LA. How was life growing up there?

Minnie Ingersoll: LA was great. I grew up in Pasadena, which is not — well, it is where a lot of movies are made, but it’s not the heart of Hollywood. My parents are academics. So, I grew up in a strong academic household. My father is at Caltech. It was just a nice place to grow up.

Alejandro: So why did you decide to go to Stanford?

Minnie Ingersoll: Well, a few things. I knew I was interested — I was kind of a nerdy kid. I liked math, and I thought I wanted to study math. I did not want to go to college across the street at Caltech. So, I went to Stanford, and I was looking for something kind of technical. At the time, I thought I wanted to do math. But at Stanford, in the ’90s, so much of the innovation and the exciting stuff was coming out of the computer science department. It was lucky that I showed up at Stanford when I did.

Alejandro: And also, computers. So, why computers?

Minnie Ingersoll: Yeah. Well, computers appealed to my math-engineering brain, and it was that I was good at programming, but also it was this aspect of having a family — not just my parents, but my siblings of academics. I actually wanted something that was touching the real world. I wanted to not be in an ivory tower, to some degree and wanted to be where things were happening in society. Computer science was full of innovation, and it was a good fit. This was before people were talking about startups, but the whole notion of startups and the way things were rapidly changing was very appealing to me.

Alejandro: As they say: nothing that kills you at the end — if it doesn’t kill you, it’s just going to make you stronger. I know that you had quite an experience here at Stanford, and perhaps something that made you stronger, as well. So, what happened there?

Minnie Ingersoll: A few things. I would say that computer science by itself was a really hard major for me. I decided to do computer science, but then ended up not doing a lot of other things. I actually went into a hard time at Stanford, where I stopped doing things like exercising and sleeping and eating healthily. I got into a really bad spiral, at one point, so not only were the academics challenging, but it was more that I let myself get too focused on — I don’t know. I got into a bad loop, and I ended up dropping out of Stanford. Not like dropping out in the Peter Thiel way, but I ended up dropping out and ended up moving back home with my parents. I thought that I was never going to graduate from school because I was in such a dark place. But, if you go back to Stanford one semester later, then instead of calling it dropping out, they call it stopping out. I managed to graduate on time. It was, like you said, a good character-building experience. Not just my own character-building, but I think it made me more empathetic for other people who are going through their own different hard times.

Alejandro: What do you think was there for you to learn?

Minnie Ingersoll: In terms of my own journey going through that?

Alejandro: Yeah, I guess from this stopping out. I think that every single experience that we have or that we go through, it leaves a lesson for us to learn. What was yours?

Minnie Ingersoll: Many different ones, and you’re right. I think it actually changed fundamentally who I am as a person. One of them was the need to ask for help and also to be able to receive help. I don’t think I would have gotten through my dark times if other people hadn’t helped me. Yet, I think when I was younger and when everything was easier, and I was in my sheltered high school Pasadena experience, I didn’t feel like I needed to ask for help. But, I think, it made me feel much more grateful to those people who reach out their hands to others. So, for me, asking for help at the times when it’s hardest to ask for help has been something that I wish I could do more of. Actually, when I get the opportunity to be a mentor, I try to help people articulate for themselves where they want to be and what they need help on because I don’t think people are actually good at articulating where they need help.

Alejandro: Yeah, and I love that because there are actually some places like Europe, in Spain, where I’m from originally, people don’t ask for help. They’re embarrassed. When you actually go out, and you ask for help, you would be surprised how people are willing to extend a hand and make a difference and help you.

Minnie Ingersoll: Yeah.

Alejandro: Really cool. So then, after Stanford, what happened?

Minnie Ingersoll: Great. So, I finished Stanford, and I got a job as a product manager. I didn’t think I wanted to code, but I got a job as a product manager at a company called LivePerson. This is early days at e-commerce, and LivePerson was a live chat tool. Think of it like Intercom or something now. This was when people were nervous about putting their credit cards into the internet to buy something online. It made great sense to me as a product manager. I was excited about it. But then, we IPO’d in March or April of 2000, right before the whole dot-com bubble burst. I don’t remember exactly. We had revenues, but we didn’t have profits. Yet, we just IPO’d. Everyone said, “Dotcoms are over. E-commerce is over. Everything’s over.” I think that we had gone on an amazing growth spurt, but it looked like we were going to have to do layoffs. So, I went to business school.

Alejandro: So, you went to Harvard. It’s amazing! Stanford, now Harvard. It’s like the CV gold. Why did you think it was the right time? And, what have you learned about going to these institutions where the network is unbelievable?

Minnie Ingersoll: Yeah, the networks are unbelievable. That was, certainly, some of what I got out of that experience, but I think now, I would go back to business school if I could because I feel I’m much more wide open to all of the way businesses, especially startups, where you’re expected to wear so many different hats, and you need to know a little bit about everything. If you don’t have a whole marketing team supporting you, you need to know a little bit about many things. It was nice to get broad exposure there. But I think personally for me, to stick on the personal front, the thing that I got the most from business school was probably a confidence that I wasn’t missing something. It’s a personal pet peeve of mine when people say either, “I’m not technical enough to understand your business.” Or they say, “Well, I don’t have a business degree, so I can’t make you a basic model for — I can’t forecast my revenues and expenses.” Or something. Both of these things, I believe, are constantly evolving what the state of technology is, and what you need to know to be successful in businesses. I think that Harvard Business School gave me the confidence to know that I wasn’t missing some secret formula, but that I could feel empowered to go forward and eventually start my own business.

Alejandro: It definitely gave you the push to join one of the biggest success stories of all time. It was a company that, when you joined, was 500 people. Tell us about this.

Minnie Ingersoll: Right. I joined Google in 2002 out of Harvard Business School. To some degree, I’m not sure it was HBS that gave me that push. When I finished in 2002, very few people were going into startups at all. Some people were going into tech, but no one from my class went to Google or even interviewed at Google, I don’t believe. Some of it, for me, was I knew I wanted to be back in Silicon Valley. Google was the biggest place I interviewed. At the time, I interviewed with Larry, Eric, and Salar, Susan, and Marissa, and people who are now still household names, but at the time, weren’t. It was a great chance to get in early. It was the biggest place I interviewed. It was 500 people, and I thought I wanted to be somewhere small. But, of course, it turned out to be a great choice.

Alejandro: All the people that I interview, they always talk about the importance of surrounding yourself with the right people. Here, you were able to see this team, and it was 500 people, but you were still able to see things at a smaller scale. How do you think they were able to assemble such an unbelievable team of people because all of these guys have gone out and done unbelievable things? So, what did you see from that?

Minnie Ingersoll: A few different things. I think one of my biggest lessons in spending a decade-plus there was the importance of hiring and interviewing. The secret of the success of interviewing — I believe there is no real secret, which is: you just have to spend a lot of time on it and make sure that everyone knows that it is a company priority. I think everyone says, and I hear a lot of entrepreneurs say that they want to build the best team, and they understand the importance of hiring, but they don’t realize that — at times, I was spending a third of my time hiring. Usually, it was probably more like a quarter, but it was, let’s call it, three hours a day, which means I’m interviewing people. I’m writing up my interview notes within 24 hours. I’m sitting in hiring committee meetings to discuss candidates, to review resumes, all of that. One of the things I learned at Google was if we didn’t get our interview notes in, within 24 hours, Jonathan Rosenberg, who ran Product at the time, would come hunt you down and give you angry looks. I learned about the time required to interview well.

Alejandro: Got it. Obviously, when you interviewed well, what was that time? For example, for a good interview, how long would that be, and what would be the most important question? Like, one question that you really pay attention to the answer?

Minnie Ingersoll: I’ll say that I think, especially in places like smaller companies. I think the most important part of interviewing is actually all the work that’s done upfront. At Google, where you might be hiring 100 people, 100 software engineers who are all being hired into the same role, maybe you don’t have to spend all that time upfront, but a lot of times at startups, each position is its own unique position. You’re not hiring ten directors of engineering, or something. So, for me, I would say the most important step is all the work that’s done upfront to make sure that you know what success looks like for the candidate you’re going to hire in 18 months, and that you and everybody else who’s going to be part of the hiring committee have agreed on what success is going to look like for this candidate. Then, once you agree on what success looks like and have agreed on what the attributes are that you think this candidate has to have in order to be successful — and then, furthermore, have crafted a thoughtful interview panel so that you know who is going to be testing for which of those attributes. Then, depending on that, the most important questions might differ based on what you’re trying to assess or what sorts of attributes you’re looking for. But, that said, if you want to know one of my favorite interview questions for a product manager, I like to ask a product manager to tell me about a time that they disagreed with their tech lead. It’s an interesting look into exactly what they’ve been doing, and also their dynamics of interaction with engineering.

Alejandro: And, also, probably it’s an interesting reaction because they’re like, “Oh, my gosh! I wasn’t expecting that.” That’s a good one. But at Google, you worked for 12 years. That’s a long time. If you had to outline or describe to everyone who is listening, out of those 12 years, if you had to describe your three biggest takeaways, your three biggest lessons, what would those be and why?

Minnie Ingersoll: I think the biggest one that I took away that’s now common-place in the Valley is asking the question: what’s best for the user? And asking that over and over. Now, it sounds trite, but it’s one of those that — my mother likes the expression: repetition doesn’t ruin the prayer, as in, you can ask this question over and over, and it doesn’t become less powerful. So, I think Google walked around asking that question, “What’s best for the user? Should we do this? Should we do that? What’s best for the user?” That was one piece that I took away is to keep asking that. Another big thing, for me, that’s very relevant now in my role in venture capital is Sergey at Google, I think, started this. He used to say, “Is this a 5-billion-dollar business?” For Google, once Google got to a certain scale, things that were small bets weren’t interesting. To some degree, I think Google resembles venture capital or venture capital fund in that Google needs to make big bets. Those big bets need to be on the tune on a 5-billion-dollar bet in order for Google to — it’s actually okay if some of those bets don’t pan out and maybe go to zero, as long as there are a few that become world-changing ideas. So, like that ability to always think bigger, no matter what I was thinking. I think Larry and Sergey, in particular, would always question whether we were thinking big enough.

Alejandro: Interesting. Obviously, this was a nice segue into what would become for you starting your own business. So, after so long and being in such a rocket ship, when you were leaving Google, there were 60,000 people. You started when there were 500. So, what happened for you there, for you to say, “I’m going to go out and do this thing”?

Minnie Ingersoll: Well, for me, my personal story is a little bit of I was on maternity leave from Google. I had been an angel investor mostly doing angel investments into my friends, who I thought were incredible people likely to build incredible businesses, but I wasn’t necessarily spending a whole lot of time vetting the business so much as knowing the teams. My friend, George Aronson, who used to work for me at Google — I remind him of this because he became my co-founder and CEO of Shift, the company that we started together, and then he became my boss. He has been talking to me about this idea that he had for a long time. I decided to angel invest in him, and it was George and a PowerPoint at the time. I angel invested in him, and I went on maternity leave. One day, he said, “You know, Minnie, I could really use your help.” The next day I worked with him a little bit, and he said, “You know, you could really help us get this thing going.” I got more and more sucked in and understood the vision much better as I got more into it. The vision, then changed, and I helped shape the vision, but it started with the tenet that buying and selling used cars is broken. It’s a huge industry that hasn’t changed in 100 years to some degree. For me, I had been telling George, “Sure. I’ll angel invest.” I actually went to sell my car myself. I thought I could sell it on Craigslist. I had a crazy experience doing that when I was eight months pregnant at the time. I gradually got more up-to-speed on the space, and we started selling some of my friends’ cars and got hooked on just moving fast and being part of a startup, which was quite different. At the time, Google was a 60,000-person company. So, it felt like a number of things that converged to make it possible in my life to take the risk and do Shift full-time.

Alejandro: Let’s talk about the early days, and especially those days where you were parking cars outside of the apartment and moving them around where there was some street cleaning.

Minnie Ingersoll: Yes. Well, I think at this point, Shift is — we’ve raised hundreds of millions of dollars. We’re a reasonably large business. I think it’s important that when we started, I was showing up at George’s apartment every day at 10:00 and saying, “George, are you up? Are you dressed? It’s 10:00.” We didn’t know exactly where things would take us but we figured we would just start buying and selling cars on Craigslist, and we would learn a lot by doing that. We would, at any point and time, have half a dozen to a dozen cars that we were selling on Craigslist, but hadn’t sold yet. If you have seven cars parked in front of your house in San Francisco, street cleaning happens once a week, and we’d wake up early and have to move all the cars. But, of course, they’re not our cars. So, you have to remember which cars are yours and where they’re parked. Just humble beginnings, I guess, is a fair way of summarizing how we got started.

Alejandro: How did you guys go about building the supply and demand?

Minnie Ingersoll: I now look at a lot of marketplaces and have thought some about how do you build that size of a marketplace, and what does liquidity need to look like. The nice thing for us was, we were fairly able to build up the supply side of our marketplace without also building the demand side simultaneously in the sense that we could acquire cars, and then if we had good cars to sell, and no one was coming to Shift.com — which at the time, we didn’t own that domain — we could still sell the cars on cars.com, AutoTrader, Craigslist, Car Gurus, or any number of existing sites. So we didn’t actually require people to necessarily know to come to us, which was a nice way of being able to essentially go to focus on one side of the market initially without having to focus on both sides of the market.

Alejandro: Got it. So, how did you guys go about building the business and especially financing the company?

Minnie Ingersoll: Initially, what we were doing was, the way that Shift model works and especially early on, some things have changed a bit, but it kind of resembled consignments as in, we said to someone who was selling their car, “We will sell your car for you. We’ll give you a guaranteed minimum price, and anything we sell the car for above that price, we will split 50/50 with you.” It didn’t require a lot of initial capital from us to buy the cars because we weren’t actually buying them. So the car would still be owned by the seller in this case. We were able to play around with this without needing much capital upfront, but our value proposition was, most people are not good at selling their cars themselves. They might post their car on Craigslist, but not even look to post their car on Auto Trader or CarGurus, cars.com, let along get their car the best exposure because there is some art to SEOing the listing sites. We raised some friends and family money and were able to get a little bit of traction with a couple of $100,000. But then, interestingly, and I see this happen to a lot of people, once we had raised half a million dollars, then everyone wanted in. Then we raised a little over 3 million dollars seed round. The first $500,000 was really hard. Even though we ended up with 3 million, it wasn’t a walk in the park by any means.

Alejandro: What is the tipping point there, because I think that you’re right. The first trench is a tough one, but then it’s like everyone wants to jump in. So at what point do you think, for example, in financing rounds, that tipping point happens?

Minnie Ingersoll: In our case, it was nice that we were able to build up revenue early. I think different companies just don’t have that luxury. But for us, we were able to buy and sell cars so we could actually generate a fair amount of revenue, even if we were selling, let’s say, 25 cars a month. Depending on how you think about it if each car is a $10,000 car, we might be doing 250k a month in GND revenue. The interesting part about that, to me, was when we decided to buy and sell cars without having Shift.com established, and without knowing what we were trying to prove, even. We said, “Let’s launch and start doing this, and we will learn a lot in the process.” We almost didn’t, actually. We were like, “Well, this is already a solved problem. There are car-flippers who flip cars all the time on Craigslist. Are we doing anything different? Are we going to learn anything different?” It turns out that we did learn a lot, but it also allowed us to refine what we were doing, show some traction, and articulate our early learnings and have revenue, which I think all of those things pushed us over the edge to get the flywheel going, which is, we had a few hundred thousand dollars, which allowed us to do a little bit like get the cars washed and detailed. But then, that was enough to get us to a point where we had revenue, and we had a fair amount of refinement of our early learnings.

Alejandro: I know that you guys had the business model. That was something that you guys really needed to get right, and that came also with some restructuring and some layoffs. What happened there.

Minnie Ingersoll: Yeah. That came a bit later. We had all these learnings. This is a very San Francisco learning, but one of our learnings was, we were doing this a lot, and we were trying to prove that people would just trust us to pick up their car even though we weren’t giving them cash for their car. We were able to prove that the consignment model did work because people were letting us show up. Even our intern could show up and look like a 19-year-old kid, and say, “I’m here to pick up your Porsche. Give me the keys.” And drive off with their car. We were able to prove a lot of things worked, like the consignment model. With that, we were able to do a good job of buying and selling cars. We got good at buying and selling cars. The very San Francisco thing is, we found that a lot of people were buying Tesla’s and that we were helping them with there — because Tesla doesn’t take a trade-in, unlike most dealers, which will take your trade-in if you have a car to sell. So we ended up in this great partnership with Tesla, which allowed us to raise our Series A, which allowed us to grow a lot. Now, we’ve grown a fair amount because we’ve raised a large Series A. We have a partnership with Tesla. We’re growing a lot, but our unit economics aren’t really working. Our NPS is great. Everyone loves us, but everyone can love you if you’re giving them $1,000 and only charging them $900. The unit economics weren’t working enough to cover our costs. Not to say we didn’t make some money on the sale of the car, but not enough to cover our costs of doing that. Yet, we had VCs. At that point, we had very legitimate Sand Hill Road investors that we just raised from. We faced this question of are we going to be able to continue to grow with unit economics that don’t work, or is that foolish? Do you believe in lean startup, or do you believe in blitzscaling? We had continued to build market share, but what we decided was, the used car business is so large, it’s over a trillion dollars, that you don’t have to have 100% of the market. You can be extremely successful with 5% of the used car sales. We decided we needed to get our unit economics working. In order to do that, we were looking to expand geographically, or do we expand in the depth of our offering? We decided to expand the depth of our offering, which is to say, in addition to just selling the car, we expanded into financing and warranties. Financing and warranties are much more difficult to sell. They require — usually, you’re in front of a computer. There’s a fair amount of calculation and sophistication in terms of the options that you can provide to a customer. They were much harder for the workforce that we had hired to do in the field. We’d had a workforce that was essentially driving cars around, picking them up, and dropping them off to customers, which is a big part of our value ad, which is: you can click a button, and we will bring a car to your house for you to do a test drive. That car had been brought to someone by someone who was essentially a driver. But once we offered financing and warranty, we needed to change our workforce. That meant that we changed our model from a sales team in the field to having an inside sales team that was sitting and doing most of the sales and customer relationships from the phone. That meant that we did a rift. 1) Our unit economics weren’t working. 2) We had the wrong people in the field. So, we had to layoff some people and take a hard look at our business. At the time, it felt reasonably existential, like we’ve grown fast. If we can’t make the unit economics work, then we’re not going to be able to survive. So, let’s retrench; let’s cut burn because it’s better to do that and have a business that survives than to keep doing what we’re doing. It was really hard because I felt extremely responsible for the people that we hired and everyone’s careers. Yet, because I felt responsible, I then also felt responsible to be the person to do the layoffs myself. That was a hard decision and a hard period in our life. Luckily, it works. Otherwise, we might not be talking today, but yeah. We did that in-between our Series A and our Series B.

Alejandro: Things definitely panned out well because the company is killing it. How many employees does that company have now?

Minnie Ingersoll: That’s a good question. I’m actually not sure. 

Alejandro: Three hundred or something like that.

Minnie Ingersoll: Two or three hundred. Yeah. Something like that.

Alejandro: It has raised hundreds of millions. Right?

Minnie Ingersoll: Yeah, that’s true.

Alejandro: Wow! So, why did you decide to leave between the Series C and the Series D?

Minnie Ingersoll: A few things. On the personal front, one was that I needed and wanted to move back to LA. So, I’m back in the house that I grew up in, which is awesome, living with my parents. So, geographically, it was time for me to make a move. But, also, the company was in a stable spot. I think my skill sets are actually best matched with doing early-stage work. I had become an angel investor and was interested in being an investor. I wasn’t quite sure whether VC was right for me, but I ended up deciding that we needed to move, we being myself, my husband, and my three kids. We moved to LA without knowing what I would do for work, but Shift was in a place, and I remain very close with my co-founders, of course. It felt like a big deal to me at the time, but I think we managed to do it amicably. It wasn’t a rushed thing. Some of it, also for me, was that I was having a third child. So, it was a good chance to think about what’s important, and we managed to do it in Shift. I was going to say they don’t miss me yet, but I’m still good friends with them. It was a good time to make a move.

Alejandro: Now, you made the move, and you made the move to the other side of the table. How is this change, and especially, how is this change in perspective because before, you were pitching, now you’re being pitched?

Minnie Ingersoll: Yeah. It’s great, mostly. I get to do what I enjoy doing, which is working with early-stage companies again. One of the things is, if you go through rocket-ship growth either at Google or at Shift, one of the things is, we made so many mistakes. What you most want is to feel like all those painful moments and those mistakes, and the successes were not for naught — that they were for a good reason and that they could be useful to someone, sometime. Working with early-staged teams, sometimes, I think, “I don’t know what I could possibly offer to this team.” Yet, when I get involved, there are many things that I’ve been through, everything from tactical things like we were talking about, like doing the hiring and doing goal-setting exercises to introductions or to perspectives. There are many things that turn out if you’ve done this for the past couple of decades, you’ve seen some stuff. I love being back at the early stages of company building and finding product/market fit before that company is larger and harder to maneuver. That early product/market fit phase suits me really well. Then, also, just the chance to hear from extremely smart entrepreneurs who come and want to tell me and educate me. I feel like it’s educating me on what they’re doing, and I get to learn so much, and then find people who I feel are mutually a great fit. Then, help them get to the next level of realizing their vision. So, we’re funding people. Usually, it’s their first bigger institutional round. A lot of people have raised, say, 500k in a friends-and-family type round, but this is their first time where they’re raising 2 million dollars, and it’s no longer raised from people they know. I feel that’s an amazing thing to be able to give someone their first 2-million-dollar check to get off to the races in building what they set out to build.

Alejandro: 100%. No kidding. Those big checks, especially the first ones, they’re always really amazing. It’s a great experience. Now, for the people that are listening, and you were touching on product/market fit. Especially for those that are still going back to the drawing board and maybe they don’t see the metrics or the retention or the product flying off the shelves. They haven’t achieved that moment yet. What piece of advice would you have for them?

Minnie Ingersoll: One of the pieces there is, knowing clearly what is the vision; what are the must-have versus what are all the pieces? What are all the assumptions that you’re making that can be loosened or revisited? Sometimes, we get stuck because we think that something needs to be solved when really, it doesn’t need to be solved. It’s not solvable, or it’s the wrong problem to solve. The one thing I would have done differently at Shift — there are many things. But one is, defining the most important thing to solve. What is our vision? It’s to make used-car buying and selling easier. And it isn’t, let’s make used-car buying and selling easier by not becoming a dealership, by bringing cars to someone’s house, and by having a flexible workforce. All of those things were things we thought we wanted to do. But when it gets right down to it, if those are intractable, then you’ve got a lot of intractable pieces. It turns out that we set out and said, “We do not want to be a used car dealership.” But what we found is in certain states, including California, we had to get our license to be a car dealership. But we tried to find all these ways around it. At some point, we said, “We’re just contorting ourselves.” I think I see that a lot of times is people are contorting themselves to find something that works, but maybe they’re solving the wrong problem.

Alejandro: Got it. One of the questions that I typically ask the guests that come on the show is, knowing what you know now if you had the opportunity to go back in time and give yourself one piece of business advice before launching a company, what would that be and why because it’s been a journey for you. Now, you’ve been through it all. 

Minnie Ingersoll: Yeah. On the personal side, I would tell people that it will be okay. It will all be fine. There were many times that were really hard. Even at Google, where everyone said, “Isn’t this the greatest place to work? Isn’t this the best job ever?” There were times when my product was delayed, and I felt like I was failing, and I didn’t agree with my tech lead. It was still hard. I think that there are times where it’s fantastic to jump out of bed, and there are times where you need to show up, tell the truth, and hope for the best, and you can’t do more than that. So, it’s the multi-decade view of the rollercoaster that is startup life.

Alejandro: Yeah. I fully agree, and now, you’re very active. You have your own podcast, LA Venture podcast, and out there seeking wonderful entrepreneurs. What are the sectors that you are specializing in, Minnie?

Minnie Ingersoll: We’re pretty broad. We don’t believe that we should be the VC in the conference room, writing on the whiteboard, coming up with the investment thesis. What we like are these big, legacy industries that are right for disruption, and then meeting entrepreneurs who understand the space that they’re disrupting, not unlike going after the used car business. But we see people in agriculture, education, healthcare, and trucking: these big spaces and someone who deeply understands the space coming to us. Then, usually, we tend to invest when there are software and data involved as the technical moat.

Alejandro: Very cool. And for the folks that are listening, Minnie, what is the best way for them to reach out and say hi?

Minnie Ingersoll: I am minnie@tenoneten.net. I really appreciate it when people check out my podcast because it’s aiming to be useful advice for founders.

Alejandro: Fantastic. Well, Minnie, thank you so much for being on the DealMakers show today.

Minnie Ingersoll: Thank you so much for having me.

 

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