TenOneTen Ventures is an early-stage venture fund. The firm personifies entrepreneurial expertise within the technology space. Their mission is to back entrepreneurs who inspire them, then do whatever it takes to help them get the job done. Minnie Ingersoll is co-founder of Shift and partner at TenOneTen Ventures. This week she joins us to share her entrepreneurial origin story, as well as some of the work OneTenOne Ventures, is doing to help other entrepreneurs.
TenOneTen Ventures is an early-stage venture fund. The firm personifies entrepreneurial expertise within the technology space. Their mission is to back entrepreneurs who inspire them, then do whatever it takes to help them get the job done. Minnie Ingersoll is co-founder of Shift and partner at TenOneTen Ventures. This week she joins us to share her entrepreneurial origin story, as well as some of the work OneTenOne Ventures, is doing to help other entrepreneurs.
Minnie's story is a fascinating one. Throughout her story, you will hear just how correctly wired she is to help early-stage startups. Her journey displays the power of understanding your strengths and going all-in on them. Of course, we have to start at the beginning. And for Minnie, the start was not one where you would have predicted it would lead her to where she is today. This is Minnie Ingersoll's startup story.
“There are many flavors of entrepreneurship. You are uniquely equipped, and you need to lean into that uniqueness.” Minnie Ingersoll
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Special Guest: Minnie Ingersoll.
The Startup Story - Minnie Ingersoll
Minnie Ingersoll: Hi, this is Minnie Ingersoll, partner at TenOneTen, and this is MY startup story.
Every wildfire began with a spark. Every superhero has an origin story. And every single startup has a moment that they point to as their beginning. And every founder has a purpose that drove them in the midst of all obstacles. THAT is The Startup Story.
James McKinney: Welcome to another episode of The Startup Story. Before we get rolling with this incredible episode, I want to share an iTunes review that was shared by Ismael Diaby who gave the show a five star rating and writing, "My name is Ismael Diaby, founder of a food recovery startup in the Dallas/Fort Worth area. We are the middleman between food waste producers and those who need it most. We pick up surplus food from hotels, restaurants and cafeterias and deliver that food to the closest shelters. I came across this podcast on LinkedIn and I'm hooked. The host's questions, the founders stories, all of it is so valuable and if you're like me and get pumped by listening to other founders stories then this is the podcast for you."
Thank you, Ismael, for the great review and also the great work you're doing. For everyone listening, go checkout surplusdonation.com to look at how Ismael is tackling food insecurity across the Dallas/Fort Worth area. And for everyone else listening, you also can have this type of ad in an episode. Just visit Apple Podcast and leave a five star rating as well as a written review. I could very well read your review in an upcoming episode, so make sure to plug your brand or URL.
All right, if you've been listening to The Startup Story for the past few months then you are very much aware of Startup Story Live. Well, it's only two weeks away. For all of you who might be new to this show, let me bring you up to speed on what Startup Story Live is all about. Startup Story Live is an epic two day livestream event with over 14 hours of incredible content to help you re-engineer and rethink about your business. I know how much the shutdown due to coronavirus impacted The Startup Story, so I feel the challenge you're dealing with. For that reason, I have reached out to so many of my founder network that have built successful companies and asked them to join us for Startup Story Live to give us practical and tactical advice that we can take into our business. I'm not talking about self proclaimed thought leaders, I'm talking about real founders who built real businesses providing real tactics direct to you. And it's 100% free to register and attend this two day livestream event. This is about entrepreneurs supporting other entrepreneurs. Look, here's a quick snapshot of just a few of the founders who will be live with us to help us strengthen our business.
Jamie Schmidt, the founder of Schmidt Naturals. Jamie attended a local recreational class on how to make her own shampoo and deodorant and in just seven years she sold her company to Unilever for hundreds of millions of dollars, and she started her business during the greatest recession the US has ever seen. You have to believe she's going to be bringing some real tactics for us to navigate this current crisis moment.
Mathew Arevalo, that cofounder of Loot Crate. Loot Crate was created out of a local hackathon in southern California and within three years of that hackathon, they grew to $100 million in revenue. In their prime, they were shipping close to 500,000 boxes a month. Matthew believes that any business can capitalize on a membership or a subscription revenue model, and he's going to share how to bring that into your business. Tell me you would not have liked to have had that revenue stream during this quarantine. Of course you would have, and that is the type of real practical and tactical advice that will be provided on Startup Story Live on May 14th and 15th.
Look, there are 14 unbelievable founders that will be joining us on May 14th and 15th and you can check all of them out at startupstorylive.com. It is completely free to register and every founder who is speaking accepted the invitation because they want to see your business become stronger in response to this virus crisis. Do not miss out on this unbelievable opportunity to learn from some incredibly brilliant entrepreneurs. Again, register for free at startupstorylive.com. All right, now let's jump into this week's episode.
Our guest this week is Minnie Ingersoll, cofounder of Shift and partner at TenOneTen Ventures. TenOneTen is an early stage venture fund. The firm is stacked with entrepreneurial expertise within the technology space, which adds to the value that startups receive when TenOneTen invests in them. Minnie's story is incredibly fascinating one because throughout her story you will hear just how perfectly wired she is to help early stage startups. Minnie's story is one that truly displays the power of fully understanding your strengths and going all in on them.
That said, her origin story is not one where you would have predicted that she would be where she is today.
Minnie Ingersoll: I definitely didn't know about entrepreneurship. I have family of academics. Both my mother and my father and my siblings are all academics. If anything, they all seemed like they were doing work that was fairly disconnected from the real world.
James McKinney: Interesting.
Minnie Ingersoll: Or it was just very academic if you will. Research heavy and publishing heavy, and I really liked people and being kind of in the mix of things. And so nope, it was not on my radar. I thought maybe I wanted to study math.
James McKinney: How many siblings do you have? Just out of curiosity, just to understand fully how unique you were in your family makeup. Two parents, how many siblings?
Minnie Ingersoll: Four siblings.
James McKinney: So there were six in the house… no seven in the house.
Minnie Ingersoll: Yeah, that's right. Well, no, actually I'll clarify. My dad's a professor at Cal Tech and so we always had grad students living with us, and we had chickens and goats. No, yeah there were a lot of people living with us.
James McKinney: So in this, I mean you really were immersed in academia if you will. And so you were incredibly different from the rest of your family. How did that play out throughout your childhood? Obviously, you weren't wired necessarily like them in a lot of ways. In some ways you were, but in some ways you weren't. so how did it play differently?
Minnie Ingersoll: Well I think everyone's unique snowflake in their way. I'll share one story from how my father used to sit behind the couch when we were little kids and he'd put on this puppet show. Each kid was a different stuffed animal, and my sister was a bunny rabbit and my brother was a squirrel, and I was the tyrannosaurus rex that came in. I always had, even when I was a four year old, I had a lot of opinions about how things should be run. I was not I don't think my parents favorite young child.
James McKinney: That's so funny. I love that. So as you're coming to the end of your high school years, I have to believe that without question in your house the next chapter was kind of written for you, like you had to go to college, correct? Is that something you had to do and did you want to do that?
Minnie Ingersoll: Yeah. I was really driven. I mean all that tyrannosaurus rex energy was something I had always and I knew I wanted to go to college, but also I was driven to go to Stanford, which is where I wanted to go, and I decided I wanted to do that when I was like 10.
James McKinney: Oh wow.
Minnie Ingersoll: But yes, all my siblings went to college and my parents went to college, and yeah it was something my mother, man my mother cared a lot about.
James McKinney: Now you said you knew at age 10 you wanted to go to Stanford. What was it about… that usually doesn't come on a kid's radar at age 10. What was it about Stanford in particular?
Minnie Ingersoll: Right. And this is in the eighties before Stanford was kind of the entrepreneurship center at all. It was that it was in California and I liked California a lot. I was not, like I'm not an east coast person. I'm wearing flip flops. We're all quarantined so everyone wears flip flops, but the notion of a Boston winter was very daunting to me. So it was California. It kind of had this we call it the duck phenomenon where if you ever go and visit Stanford everyone is out like playing Frisbee. But that's the duck which is on the outside. On the surface, everyone's kind of skimming along and looks effortless, but actually they're paddling really hard underneath. But that sort of feeling of being outdoors and playing Frisbee all day, I thought that was what Stanford was all about.
James McKinney: That is so funny. I bet you were definitely exposed to lots of different colleges being just in the household you grew up in. You were probably just exposed to the culture of university life and what each school had to offer.
Minnie Ingersoll: Yeah, although because my dad's a professor at Cal Tech that would have been free and I was very exposed to that. None of my siblings went to Cal Tech and living across the street from a college is not what you think of when you think of, "Oh, I want to go away to college." So I knew I would go somewhere other than Cal Tech.
James McKinney: what your parents should have done, they wanted tuition to be free they should have moved two hours away and just sucked up the commute and be like I'm living away from the house.
Minnie Ingersoll: You know what, I still wouldn't have gone to Cal Tech, although I love it. I love it. It's just not for me. It's not a good fit.
James McKinney: When you went to Stanford, what did you think you wanted to do? In your mind, what did post Stanford look like for you as you were entering Stanford?
Minnie Ingersoll: No idea, no idea. And consistently I'm one of those not well planned out sort of people. Not my strength. Yeah, thinking in advance and figuring that out, so maybe because my parents were academic also I didn't know the difference between what is a management consultant do, what does a business person, what are the different roles in business? I don't know the difference between marketing and PR, or product marketing versus marketing. All those things, I didn't have any concept of what they were, let alone what I wanted to do, but I wanted to what the smart people were doing if you will, or kind of I wanted to be in the mix of what was exciting, but I didn't have a good sense of that.
James McKinney: See this is interesting. From someone like myself, I was raised by an entrepreneur, immersed in business growing up being a part of my dad's print shop and just kind of seeing all that entrepreneurship had to offer it's hard for me to think of what it would be like to go somewhere and not have an understanding of what opportunities there were in business. And so for yourself, I would love to just kind of know if you can remember what were some of these moments where your eyes are just opening up to the opportunities of wait I can do that, oh that's in business, that's entrepreneurship. Do you remember any of these a-ha moments just within your time at Stanford? Like wait that's a career?
Minnie Ingersoll: Some of it was amazingly… Stanford was, especially when I went, I graduated in '98, it was still kind of sheltered in a liberal arts sort of way where there's still, you know I studied computer science but I also took like Spanish literature. It took me a long time. It wasn't even at Stanford where my eyes started that popping sort of thing. It took me a long time when I was actually in the working world where before I started to understand how business worked. I still feel like I am learning how business works because no, definitely at Stanford I still did not get a lot of exposure to understanding what the different avenues were.
I will say that it became very clear to me that the math department didn't have the energy again that the computer science department had in terms of just innovation that was going on and being able to take what was kind of going on from the grad students, the professors, and apply it to the world. And just have news stories be written about the companies that were coming out of the math department was not happening. That was eye opening to me. And again, one of the things I've always been good at or enjoyed doing is looking at what are the smart people doing and where are they going. There was so much to admire and so many smart people moving into the computer science world, that innovation. I remember getting my email account for the first time and that being kind of eye opening.
James McKinney: It's interesting too because you said you graduated in '98. Obviously I think Amazon considers its founding to be '95 or '96, so you really were, the internet was really starting to become a resource for things beyond just information if you will. Do you remember what you were thinking, okay I'm going to go into computer science, that's my focus, and I think that's what I want to do or this area of computer science is interesting to me. Coming out did you just think I want to just be a database developer, I wanted to be front end? Where did you think you wanted to play?
Minnie Ingersoll: By my senior year, I was pretty good and pretty driven so I did pretty well in school and got mostly A's and that sort of thing. But by my senior year I started to really I was paddling really hard. That duck phenomenon, it was hard and I started to think that maybe I was not meant to be a programmer. Maybe there were just, maybe I'd kind of tapped out on my skill level of just being able to hold as much in my head or understand things. In retrospect, I can name my classmates that I was sharing an office with and they are people that you will have heard of now because they are Marissa Mayer, Adam Nash who was the CO of Well Front, John Lilly, I shared an office with Adam Nash, John Lilly was his best friend. John Lilly's an investor at Greylock so in retrospect, looking back on it, maybe I didn't think I was the smartest but partly because I was comparing myself to this amazing peer group. And so many of my Stanford classmates are now really running huge companies or investing in important companies. So that might have been some of it.
But anyways, I decided that maybe I was not meant to be a computer programmer, not because I was worried I couldn't hack it but it wasn't quite as fun for me. I liked programming but not all day.
James McKinney: You know, I have to ask this question just because of the people that you shared an office with. You know obviously there's this persona about Stanford and technology, and rightly so, but do you think now in 2020 aside from the quarantine, the graduating class, if I'm having this type of conversation with someone who is graduating Stanford 2020, 10 years from now do you think they will be able to have the same type of population of recognizable names who have done amazing things within technology, or do you think that was a capsule in time?
Minnie Ingersoll: There was one piece of it which is I got involved in the Stanford section leader program, and these are the people who are able to be essentially TAs for the computer science department while they're an undergrad. I still when I meet people who went through that program, I still think that they are really top people who I want to hire, not just because they're good programmers but they spent the effort to figure out how to be good teachers as well.
James McKinney: Interesting, okay.
Minnie Ingersoll: The big change is that it's not a black box where you really have to be in Silicon Valley or at Stanford in order to be part of the ecosystem or to know how entrepreneurship works, and that has changed dramatically. So I think it used to be that you kind of had to be in the mix in order to be in the mix, and now you can start a company in Lincoln, Nebraska and still be a successful entrepreneur.
James McKinney: Yeah, interesting. Awesome, awesome. So you're surrounded by incredible people at Stanford. Your time at Stanford's coming to an end. You're graduating. What is that next step for you?
Minnie Ingersoll: Well, I decided maybe it was time for me to like, I was 21. I think I just turned 21, I was like I'm going to go live in Manhattan, so I did that. But I joined a company that was a startup as a product manager, and a product manager was a really good fit for me, but that was kind of arbitrary. That was like someone who I thought highly of was running the product organization.
James McKinney: What was the startup?
Minnie Ingersoll: It was called Live Person, and it's essentially like a chat window that pops up when you're about to do checkout on your ecommerce site. So the idea was the internet is becoming this huge thing, this is like '99 or 2000 and people are, they're still hesitant to put their credit cad in at checkout so it's this whole abandoned shopping cart phenomenon. And that made a ton of sense in '99. It turns out the company is still around, but it IPO'd in March of 2000 and that was right I think the whole world, the dot com bust happened in April or something, so we IPO'd, we were not profitable, and we'd grown from like 20 people to 200 people and I think it was looking like there was going to be a big round of layoffs. That was my right out of college experience.
James McKinney: So coming out of Stanford though, you said you had respect for was it the founder or that's why you joined the startup coming out of Stanford?
Minnie Ingersoll: I think he was the head of product.
James McKinney: Head of product, okay. So it really was the relationship as to why you jumped into the startup space. So it wasn't the sex appeal of the startup industry at that time, because really internet was super hot then but you're right, the bust happened and it decimated a lot of things.
Minnie Ingersoll: I really didn't know. I looked at everything from consulting to doing all sorts of different things. So this was just, it was a lucky choice. Because product management turned out to be a good field. I didn't study product management. There weren't any product management classes at Stanford, so I had no idea what it meant to be a product manager, so it was lucky.
James McKinney: I guess because there wasn't much in the way of product management from an academic perspective we'll call it luck, but I can definitely see your personality of wanting to be in the middle of things fitting so well n that product management role. Just for a little bit of foreshadowing, because now you're an investor, when you look to investment do you look at who's running product management or do you care more on the developer side?
Minnie Ingersoll: Like if I'm evaluating a company?
James McKinney: Yeah.
Minnie Ingersoll: I want to see a balanced team is usually what I'm looking for, meaning the major functions are actually covered with executives or people who I think can scale in their role. Not scale infinitely in their role because I think that people who are good fits for building a company to a $10 million run rate business are different than sort of going $10 to $100. But yeah, I want to see strong product people. I actually increasingly I think differentiation comes from product and design, whereas before when we were still understanding how the internet worked you could have more technical differentiation. A lot of products now, it's in the user experience.
James McKinney: Oh, absolutely. I love having conversations about user experience, but that is a whole other podcast episode. It wasn't until I got acquainted with some very smart and creative people that I fully understood how important on so many levels the UX is. It can truly take an amazing product and just ruin it completely.
Minnie Ingersoll: Yeah.
James McKinney: And so as the dot com booms happens, you exit your first startup, your first out of college job. What was that next step?
Minnie Ingersoll: I went to business school. So I went to Harvard Business School, again because I really I still didn't know what I wanted to do or be, but I visited the Harvard Business School campus and was like this is amazing. This is like sort of like it's what it looks like on postcards. Like when you think of sort of brick buildings and snow covered, and it's the Charles River. I applied and then they let me in so I thought well gosh, if they let me in I'll probably go, and then I got in. So I went there and it was all of that classic east coast sort of feel to it.
James McKinney: You got over your aversion to cold winters, that's what you're saying?
Minnie Ingersoll: No, I didn't really. It was still, that was really hard. That was really hard. It just looked nice on a postcard. It was really f-ing cold.
James McKinney: So in a previous episode we had a founder that had an idea for an online community and it wasn't until he went to business school, and I don't think it was Harvard but it was another high echelon business school. I know Harvard Business grads probably say there is no other equivalent echelon but there is. And it was in that season at that school that he really got a chance to flush out the business side of his startup. How impactful was your time at business school to help you understand the business side of this world that you had really only had a couple years exposure into?
Minnie Ingersoll: it was important but maybe in different ways than I had expected. I hadn't had business experience and coming out of Harvard, I felt like oh there is no secret handshake to how business works. I'm not missing the secret formula for how to build a startup or to run a business, or to be a product manager, or anything else. Because at least you could say I was exposed to one of the best business programs and if I didn't learn it there, well I'm going to have to make it up and figure it out. But I came out with a lot more confidence that I wasn't like missing something about how to build a business model. That was useful for me, especially getting into starting my own business.
James McKinney: Yeah. So after Harvard what was your next step?
Minnie Ingersoll: I went to Google.
James McKinney: Before we continue on with Minnie's incredible startup story, I want to expand a bit more about the incredible opportunity you have with Startup Story Live. Many times I hear from listeners just how fortunate I am to sit with these incredible founders, to pick their brain, and to learn directly from them. And I can't argue, I am incredibly fortunate but that is exactly what Startup Story Live is going to be providing for you. Every single founder will be live and there will be a Q&A session with each of them.
You get to sit with founders like Jason McCann of VariDesk, now rebranded as Vari. Jamie Schmidt of Schmidt Naturals which she sold to Unilever for hundreds of millions of dollars. Christina Stembel from Farm Girl Flowers. You might recognize her from the Capital One commercial series that's everywhere. Matthew Arevalo, cofounder of Loot Crate which grew to $100 million in just three years and pretty much put the subscription box business on the map. Meghan Asha of FounderMade. Davis Smith of Cotopaxi and so many more. The list of founders that we have for this two day livestream event is unreal. This type of opportunity to get direct access to these amazing founders would cost close to $1000 in any live setting, but at Startup Story Live it's absolutely free. Yes, the entire livestream and Q&A opportunity is free. Do not let this opportunity pass you by. Visit startupstorylive.com for all the details and to register today. All right, enough of the announcements. Now let's get back to our episode.
James McKinney: After Harvard, what was your next step?
Minnie Ingersoll: I went to Google. So all my classmates were graduating with jobs. The banks and the management consultants and all that, they recruit like five months ahead of time. But startups, no startup is saying, "Oh, I want to hire someone in five months," right? And so I was pretty sure, I did the Harvard Business School on the east coast and I was pretty sure I wanted to go back to startups, and I was pretty sure I wanted to go back to the Bay Area, it made that clear for me. But I wanted to go to a small startup. This is 2002. There were no small startups coming to the Harvard Business School campus thinking oh I want the MBA. They still make fun of MBAs. I mean, I do myself sometimes, from time to time.
But so I just decided well one, I didn't get a job and two I sort of decided it's a lot easier to go find a hot startup if you're in the area you want to be. If you're in Silicon Valley you're talking to, you're networking essentially. And so I moved back. I moved to San Francisco and started to just trying to figure out what's a hot company right now. Again, sort of luck I ended up at Google kind of through my mother. I was using Google so I was certainly familiar with Google, but my mom knew that I just finished business school and didn't have a job, so she sent me a screenshot or something from the Google homepage where they put up an ad that said, "You're brilliant. We're hiring." And my mom sent that and she said, "Minnie, Minnie, you're brilliant, they're hiring, come get a job."
James McKinney: That is awesome. Oh my goodness. It's so funny. There's so many stories we've heard that are so similar to that, but on the dating side. Gotta love moms, gotta love moms.
Minnie Ingersoll: Yeah. My mom would have chosen who I married too. But yeah and then you know Google was small. It was 500 people. So then care of my mother I sort of thought to reach out to people there, but then I interviewed with Marissa who I'd known from Stanford and Larry and Sergei, and Solar, and Susan Wojcicki who are still at Google, they're still running well in different roles but that was my interview panel. So then I was like wow, these people really are amazing.
James McKinney: That's incredible, that's incredible. So I definitely want to unpack a lot of time that you spent at Google, but I have to ask one question back to your Harvard time before we get into the Google space. You're finishing Harvard and all your peers are being recruited by the management consulting firms. One of the things that we talked b in our time together is this idea that you want to be in the middle. You want to be part of a lot of different things. Management consulting has that opportunity and I'm sure they probably sold it or tried to sell it to you in many different ways. But you said something very clear that you wanted to be with startups. What was it about startups and how hard was it to not chase that management consultant check? Because I know that the recruiters wave that in front of a lot of MBA students as well.
Minnie Ingersoll: Yeah. A few things. Both my strength and my weakness is just doing things. I love doing things and it's also a part of my journey through adolescence or something is like my job was always as a camp counselor. I love just getting in there, doing things when they're not really well planned out. I kind of chafe at all the strategic stuff and so management consulting was really not a great fit for me because I'm also really good when you're allowed to kind of move fast, iterate quickly. I think management consulting is more like talking to the Fortune 500 companies about long term plans and matrices and all that.
James McKinney: Got it. So you get hired at Google. Let's get back to your Google days. You get hired at Google. What was your first project? Did you get hired as product manager like you were before?
Minnie Ingersoll: Yeah.
James McKinney: What was your first product that you were managing?
Minnie Ingersoll: So I worked on the billing system. The billing system-
James McKinney: It sounds super sexy already, let me just put it out there.
Minnie Ingersoll: I know, I know. You know, I always was because you always have to sell things, and you're always trying to get more engineers onto your team. So I was always trying to sell it as a super sexy project. But in 2002 we were still a couple years pre IPO and we knew that we needed to go public at some point. We wanted to but we were not at all Sarbanes-Oxley compliant and we were just, our billing system, we needed to close the books every month and that involved getting the logs from servers that might be in Hong Kong serving Chinese traffic to Japanese advertisers, get those logs, and figure out what each advertiser got. And even if a server went down, figuring out how do we turn this into a bill in Oracle in a couple days. And you couldn't do things like retrieve the logs in spreadsheets and email them to each other.
So figuring out how to turn that into an automated system and still provide our advertisers with the flexibility that they wanted, because advertisers want to advertise only on weekdays, not on weekends. But if your server ends up serving a few extra clicks on times they're not looking for… so just unraveling that whole system. Not that I personally unraveled it all but working on that for a number of years was actually a super interesting project.
James McKinney: This is fascinating. How old was Google at the time of you starting that project?
Minnie Ingersoll: You know, when I joined I think they were having a birthday party and it must have been like four or five. I think Google started in '98.
James McKinney: Okay so we'll say four or five years. I want all my entrepreneurial audience to be hearing this. I think there's so many times as entrepreneurs we get hung up on trying to get all of our ducks in a row before we launch a product. So you're saying, if I'm understanding correctly, Google launches ad words or whatever. They probably didn't make money, hve any type of revenue lying down for the first couple years, so I'm going to assume a little bit that ad words was its first revenue line item. So they launch ad words without all the back end trying to figure things out from a billing perspective.
Minnie Ingersoll: Yeah and it was a real challenge. There was also a tension there between these sort of self serve products and then for the large advertisers actually having account managers managing that, and there was a real push from people saying, "Look, I can bring in an extra $10 million in revenue if we can offer an advertiser this. I can bring $10 million if we do that." But figuring out all the points where things would break. And I think especially when your business is booming there is no chance to solve all of those problems. And so our approach at Google a little bit, again going way back, was if you under bill the advertisers they won't complain. So we were definitely trying to cut any corner we could.
James McKinney: It's kind of crazy when you think about it because you talk about going way back. Yes, 15 years in technology world is way back. But when you think of just how big Google is now to our culture, not even the company side but the fact of how integrated our way of living, our daily life is in Google and to think just 15 years ago papers and Excel spreadsheets were flying all over the place trying to figure out how to bill to advertise, unbelievable. Incredible to me. So you worked on that project for years, but you were at Google for I don't know 11 or 12 years I think.
Minnie Ingersoll: True. So I did that for a while and then I ended up teaming up with Chris Saka who's now a very well known investor. He started Lowercase Capital, but at the time he was a lawyer at Google. We started sort of being entrepreneurial within Google which was fun. We both had different jobs but one of the things we did circa 2006 is we were just looking at interesting technologies that we thought Larry and Sergei would get excited by and one of those was mesh networks that you could do Wi-Fi where each Wi-Fi router didn't need to be connected to the internet, but it could kind of connect to another one. Anyways, we got excited about this. Essentially we were at a fundraiser if I remember correctly at Ron Conway's house for Gavin Newsome and we ended up getting Gavin Newsome saw the possibility. I think it was the next day Gavin announced that the city of San Francisco was going to have free community Wi-Fi. I think it was one of those where I was like oh man, I have a different job but I'm going to have to scramble to make sure we didn't completely over promise on that. So then that became a full job of mine, so figuring out munity Wi-Fi for San Francisco which became a whole mess of Google at the time really didn't understand. It was really tech focused and we just hadn't thought about interfacing with government, how cities work and how real stakeholder management. Now Google of course has more lobbyists than anyone, but at the time that was a new discipline and so we brought a bunch of signal propagation engineers to the city council meeting.
James McKinney: Obviously that was Wi-Fi but did that become the foundation for what we know now as Google Fiber?
Minnie Ingersoll: Nope, that was a different initiative but yes it was the same group that launched those things. So Chris and I ended up calling ourselves the access team and it grew beyond just us of course. But the access team did end up launching Google Fiber. That was one of the things there. The early story there of Google Fiber was we were doing that really to catalyze the industry more than we were doing it to build a full business model ourselves, and actually congress had put out a request for proposal on how to build high speed internet. We had been writing comments on that proposal and finally Sergei was like, "Why are we writing comments and not just doing it ourselves?" Okay.
James McKinney: What is the timeframe it's going to take to bring that into we'll say rural America?
Minnie Ingersoll: Yeah. I don't exactly know the answer but let's just say it's more than five years. It's a five to ten year endeavor, that sort of thing. But that kind of goes to the way Google operated. Looking at it from my vantage point now, I think of Google as similar to like a VC firm in some ways, which is every bet that Google makes needs to be a multi billion dollar bet. It has enough cash but it can't spend its time in resources on things that aren't $5 billion or bigger potential outcomes, and it's okay if some of them don't succeed which is fairly similar to how VC funds operate.
James McKinney: Now you said you had to pitch Larry and Sergei on the mesh idea. Obviously you've been out of Google now for five or six years, i don't know I forget exactly the timeframe that we're talking now. How long have you been out of Google? Might as well just put a timestamp on it.
Minnie Ingersoll: I left in 2013.
James McKinney: 2013, so you've been away from Google now for seven years. Are Larry and Sergei the ones being pitched or is there a bureaucracy into how we pitch these internal unicorn projects?
Minnie Ingersoll: Definitely there's a bureaucracy. But some of it is as you say I stayed there for a long time, I also knew how to navigate the bureaucracy. Some of what a product manager at Google does there is some aspect of it that is stakeholder management.
James McKinney: Oh, absolutely.
Minnie Ingersoll: And I learned who the stakeholders were, who my champions were, that sort of thing. So back in the day it used to be called Google Product Strategy, GPS, and GPS was held every week in the same conference room. He would go and pitch Eric, Larry, Sergei at the time. So this is back in the day. There was different bureaucracies like no manager wants to bring in their junior product manager who's just going to waste people's time if they haven't thought through all the questions. So I think at the time I was reporting to Susan and she would decide who from her organization needed time that week in front of Eric, Larry, and Sergei.
James McKinney: Got it, okay. So your time comes to an end at Google, you're doing amazing things. Why would you leave Google? An incredibly entrepreneurial environment, why would you leave it?
Minnie Ingersoll: A few things. One, when I left I'd been there a third of my life.
James McKinney: Got it.
Minnie Ingersoll: So there was that. And I used to say well yeah, I'm being entrepreneurial within Google. And then I went and started my own company, Shift, and was like oh this is entrepreneurial. You're not entrepreneurial really if everything is kind of provided for you.
James McKinney: Yeah, it's totally different when it's your bank account.
Minnie Ingersoll: Oh yeah. And launching a product is a different skillset than launching a company. They have some similarities. You have to launch these things. I got very hooked on the whole idea of launching a business, which required me to stretch in all different ways than just launching a product.
James McKinney: So your reason for leaving Google is that you actually wanted to launch a business?
Minnie Ingersoll: No, it was more the boiling of the frog sort of thing that I got into it. I was on maternity leave and I had written an angel check to my friend George, who's now my cofounder George, but at the time he was just a close friend of mine. Then I went on maternity leave and he asked me to help him get the business started, so that was my naive way of getting completely sucked in, and I just got more and more sucked in as time went on. But it was clear to me pretty quickly that I was going to bed thinking about Shift, waking up thinking about Shift, but I didn't set out to do that, no.
James McKinney: So let's jump into the chapter that is Shift. So can you unpack what Shift is for our listeners?
Minnie Ingersoll: Yeah. It's an online marketplace to make buying and selling used cars better user experience.
James McKinney: And this was in 2013?
Minnie Ingersoll: Yeah, that's when we started it.
James McKinney: So 2013, so from a framework there wasn't, I'm trying to think who might have been competitor in 2013. What other resources were there? eBay motors maybe.
Minnie Ingersoll: Well, there was BB, Carlypso, Car Gurus, Carvana, Vroom.
James McKinney: Carvana was 2013?
Minnie Ingersoll: Maybe 2014, like it was pretty close. It was pretty similar. Yeah, they were pretty contemporary with us.
James McKinney: Okay. So what was it that drew you into that space? Now obviously your cofounder George, he was the one that brought you into the fold but we tend to not go into something that we're passionate about so were you passionate about the problem you were trying to solve? Or were you passionate about just trying to build a business that was new to you? What was the passion for you?
Minnie Ingersoll: He was definitely more passionate and steeped in the business itself. But it made sense to me from an angel investment, think of this as like a huge market, trillion dollar plus market in the US. 70% of people still post their car when they're trying to sell their car on Craigslist and do a horrible job of selling their car. So it just seemed like a lot of opportunity there, both to help people sell their car better but also to help them get financing. The more I got involved the more I became passionate, which that is not true of everything.
James McKinney: So as an investor now, because you're not with Shift, you're a VC, so as an investor what is more important to you, the problem to be solved or the founder's passion to solve that problem?
Minnie Ingersoll: Not even just the founder's passion, but also the founder's expertise which often go hand in hand in that someone whose lifework is around, they've built up a franchise of daycares and now they're building software to serve their franchise, and now they just need venture money to scale the work they've already been doing, but you know this is their life work. That expertise and passion are often tied, and I really look for someone that knows the industry extremely well. You could argue to some degree I didn't have that myself at Shift, but I also look for a balanced team and it's rare that you find the whole team necessarily is coming from the same perspective or the same background.
James McKinney: Yeah. So as a cofounder were you part of the pitching circuit? Because that's part of the startup story is the funding element of it. Were you part of the pitch circuit or were you more on the product side?
Minnie Ingersoll: I was definitely part of the pitch circuit. There was me, George, and our other cofounder Christian, he was the CTO. He preferred to be heads down. But certainly in the earlier rounds especially, our seed round was my friends and family. Our Series A was really marching up and down Sandhill Road, going to each building, going upstairs, going downstairs, figuring out which VC you're going to run into the hallway of the other VCs office, and really getting to know that circuit for sure.
James McKinney: So in 2013, 2014, we are five years away from the worst recession that we ever saw in our country. Funding had to have been challenging. Obviously we were recovering, but it still had to be challenging. Was there ever a point in your early days at Shift where you thought this just isn't going to happen?
Minnie Ingersoll: Yep, multiple times and sometimes multiple times a day. But each funding round was hard. I was not sure just in raising our seed, the first $250K was extremely hard, and then once we'd raised $250K it was quite easy to raise another like $3 million essentially. And then our Series A, I didn't really know what Series A investors would be looking for but we had some traction just doing things with duct tape. Then we ended up into a Tesla partnership, which then really helps us close our Series A but that was again a bit of luck and opportunity. But yeah, we went through a riff. We had to lay off a bunch of employees where I thought that might have been an existential moment, so there were a lot of those.
James McKinney: So in the scaling and growing of Shift, how long did it take you guys to get to revenue? And then when you say you had moments of traction or points of traction to show for your Series A what were those points? Then you mentioned a partnership with Tesla. Was the success built on the partnerships that you guys were able to negotiate and close, or was it more just the business model was showing? What was the key success point in order to get that Series A?
Minnie Ingersoll: At first we didn't have any funding, so we weren't like, we didn't have a warehouse for our cars. We were parking cars on George's street like outside his apartment. But what we were able to do is we were able to just sell cars. We didn't really know, like selling cars on Craigslist is itself problem. It's not like we were doing anything interesting. We either got the advice or had the intuition that doing things you learn where the problem is, or you learn just by doing. So we got to something like selling 30 cars a month. If we were selling 30 cars a month we were already doing about call it $300K in top line revenue a month. And that's actually starting to show some real volume. It's showing at least that we can manage some amount of top line revenue to our investors, that started to look interesting.
And then we ended up finding in the Bay Area that Tesla had no way of managing trade-ins for customers who were buying a Tesla. They had no way of managing trade-ins. So if someone had a used car, and we just thought you know what we can solve that. We can be the trade-in partner for Tesla. Now, Tesla didn't give us permission to do that initially, but we just thought we could hang out at the Tesla dealership and find all the customers who were walking in there and needed a solution for their trade-in. some of it was yeah, we were able to have revenues that caught the attention of Series A investors.
James McKinney: Those stores of just hanging out at a Tesla dealership, those are the startup stories that I love, just those gritty pure determination opportunity moments you're like what a second.
Minnie Ingersoll: We brought them donuts. That's why they let us stay.
James McKinney: See even at a Tesla dealership, car sales people are still car sales people.
Minnie Ingersoll: Yeah. Yep.
James McKinney: Love it. So you are no longer with Shift today. You are with TenOneTen Ventures. What was the catalyst for exiting Shift? And just let me ask the question, are you out of Shift or just no longer working with Shift and into TenOneTen?
Minnie Ingersoll: Yeah. So I'm now in LA and as you said a partner at TenOneTen, and Shift was really a San Francisco based company. Also, I was never on the board of Shift which was interesting.
James McKinney: Why is that?
Minnie Ingersoll: Well, George who is my cofounder, we actually ended up with four cofounders. Actually at one point we had five cofounders, and not all of us were going to be on the board. In some sense, maybe I was naive and if I did it again would I have demanded a board seat? I probably wouldn't have but I would have given it more thought. But as it was, George was the only one of us that joined from the executive team, and I actually think it was a smart move by George and it worked out well. But yeah no, I'm no longer at Shift. Just friends with him and definitely still an equity holder, so try to be helpful whenever I can.
James McKinney: But what was the reason for leaving?
Minnie Ingersoll: Some of it was a desire to be in LA, and that was a very strong desire to move to LA which I've been trying to do for a decade now. And some of it also was that I really think that my skills are best suited to that early startup stage where it's not clear what to do and you need someone who's just iterating really quickly. And when things need to be more reliable, accountable, predictable, strategic, I think that there are managers who are better able to do that. So some of it was maybe I didn't feel as well…. My skillset wasn't as well suited and I was also having a third baby, and that made me sort of think about what do I want to be doing. I had three kids under the age of four and thought it's getting a little much to juggle, and so maybe I'll take a chance and think about where I want the next decade of my life to be.
James McKinney: Why an investor versus another startup for yourself?
Minnie Ingersoll: Well I agree with what you were saying about the best sort of startup founder is someone who is completely passionate about it, knows the space cold. I didn't have something that was bubbling out of me that I needed to dedicate the next couple decades to, and having just gone through the entrepreneurial experience I realized that it does need a decade long horizon, and I didn't have something like that. At the same time, I love being entrepreneurial in my day to day life. My partner at TenOneTen calls it my initiatives. So I still get to do all my initiatives, but just as part of TenOneTen. And TenOneTen is an early stage fund. There's only three partners. There's only five of us who are core members of the team so it still feels like a startup. There are a lot of similarities between being in a five person startup and a five person venture fund.
James McKinney: And what is a startup for a venture fund look like as opposed to how we think of startups whether it be a brick and mortar business, an ecommerce business, a SAS business, whatever the case may be. We can probably understand that framework a bit, but what is a startup world and a venture fund look like?
Minnie Ingersoll: We sit in a co-working space most of the time. LA's big so sometimes we go and sit at one of our portfolio companies that's a 200 person company and we sort of sit in one of the corners and drink their coffee. We're always doing fundraising. So similar to a startup we have to do our own fundraising. Big component of what we're looking at. We're still putting in processes for like what should our CRM process be for how we manage it's not quite our customers but it's the companies that are coming inbound. We don't have great processes in place and things are still being figure out. What should we be looking at a weekly, monthly, quarterly basis. All of that stuff has… and all the flexibility of it's not a big bureaucracy. I started my own podcast, as you know, because it was an initiative.
James McKinney: That's so great. When I think of a VC fund, and one of the things I heard recently from Reed Hoffman is 90% of his portfolio they're platforms. He's a big believer that your solution needs to be a platform, where people on your platform are making more money than you're making, that type of scalability. Is a VC fund similar to a platform? Because you have the investors who should be making a tremendous amount of money if you will, but then you also have to worry about deal flow. So you have two sides to the equation that you have to navigate. Isn't that representative of a platform?
Minnie Ingersoll: Kind of, but it's not a scalable platform. I mean I haven't given this a lot of thought, but VC is fundamentally a services business and a personal business. The vale that I bring to my portfolio is really what I can bring, how many hours are in my day. Now, some of that we try to make scalable. Some of like the benefits that we offer to our founders. But a lot of it is still a services business that I don't think scale.
James McKinney: Interesting, okay. Excellent. So from a business perspective, your job, your role, your focus is more investors, more deal flow to get that investment out. You don't want to be sitting on those funds.
Minnie Ingersoll: Right, that's true. And also helping my portfolio companies, because I do seed investing, helping them raise their Series A or their Series B, and making introductions for them. It turns out the thing that's surprised me the most, there have been many surprises but one is that it's a sales job. A lot of it is a sales job and I'm formerly a product manager, and just learning I'm always selling my portfolio companies in addition to selling myself to potential portfolio companies and raising money.
James McKinney: Interesting. And from an investment perspective, what, since you are seed and it's actually two questions that come from that understanding, what are the size checks that TenOneTen writes?
Minnie Ingersoll: Between half a million and $1 million.
James McKinney: For a seed?
Minnie Ingersoll: For a seed, but usually someone is raising between $1 - 3 million. And also this is pre COVID numbers. Pre COVID numbers, people were raising between $1 - 3 million for their seed round that we were investing into. And we're not a pre-seed fund. Usually somebody has already raised call it something like $750K in a pre-seed round.
James McKinney: Got it, okay. Okay. So you're that half step before the Series A basically.
Minnie Ingersoll: Yeah, and when I was raising money in 2013 usually there was one round before a Series A and now there's two.
James McKinney: Interesting. One of the things that I've read recently is the longer runway before you get to a Series A, like it just keeps getting pushed back longer and longer. They're wanting to see more again whether it be revenue, more client acquisition, more traction. Just wanting to see more before you get to Series A. So I can understand that need for the two between the friends and family and the Series A, because it's going to take longer. Why do you think there is that delay before Series A? What is happening now in the space for our startups that are listening that A is just farther down range?
Minnie Ingersoll: I think it's just that as I say we're investing into a $3 million round, you might have called that a Series A. so I think just the names are changing. So now I just say define it by how much money you're raising. So I'm doing a round right now to raise $3 million. Call it that rather than trying to call it an A or a pre-seed or a seed.
James McKinney: Okay. And what are your areas of focus for investment?
Minnie Ingersoll: We historically have invested into software and data heavy businesses, so where there really is a software or data as a mote or as a differentiator as opposed to say a software enabled business. We sometimes call it like an engineer turned entrepreneur. It's what all of our backgrounds are in. All of us have technical degrees. It's also a growing area in LA which is interesting because LA traditionally had sort of the reputation of being a more ecommerce or digital media entertainment, but now there's entrepreneurs building all sorts of businesses everywhere and so we're trying to carve out that spot as the sort of techie fund in LA.
James McKinney: What portfolio company do you have that would be a great example of that data as a mote?
Minnie Ingersoll: I have one that's a good data company that's kind of a classic investment for us, it's called Descartes Labs. They take satellite data, interpret that data for agriculture. They actually have different customers, agriculture is their biggest one, Department of Defense. So taking big amounts of data, having to find insights in that data.
James McKinney: Interesting. Since you've been there, what have been some companies that you've invested in specifically?
Minnie Ingersoll: I did an investment in a company called Strattic and I joined the board which we sometimes do, sometimes don't do. Strattic is taking your WordPress website and converting it into a static page. There is this big movement for static websites because they are very fast, they are unhackable, and you don't need developers to maintain static pages. But the trick with Strattic is you still get the WordPress front and you don't then need a developer to create a static page for you.
James McKinney: interesting.
Minnie Ingersoll: And they're really catering to the mid market to larger customers who have a lot of content on their websites, but aren't necessarily tech companies. It turns out it's an interesting technical challenge. Like I was telling you there's often a technical challenge because you sort of have to compile the WordPress site into a static page. So it's a good example because there's real technology involved.
James McKinney: Incredible. Now what was their founder's background, out of curiosity?
Minnie Ingersoll: Well she is the incredible woman. They are based in Jerusalem which is interesting, not our typical investment. But she actually I think was struggling to raise some in Jerusalem, maybe partly because she was a woman which I think is harder I think especially in some locations. She had started a company beforehand that was a digital agency that managed WordPress sites. Her whole career, she's really an expert in WordPress.
James McKinney: Okay. You brought up a good point about the challenge of a female founder. In particular, we were speaking specifically about raising money in Jerusalem but there is something to be said about the overall challenge of a female founder raising money. On the investment side and as a female, I suspect that you obviously don't have that bias probably but what are you seeing in the VC space that is being done to correct some of the biases towards female founders in the portfolio balance if you will?
Minnie Ingersoll: It's both hard but I also feel optimistic and I like to leave people with sort of an optimistic message about it which is because I am a female investor, because I am a female founder, I do get a lot of opportunities put in front of me. I get asked to speak on panels or serve on boards, or be part of events partly because people are aware that having women, people of color, other underrepresented groups up on stage or more visible is really important. I think you're doing a podcast, I'm sure you're deliberate about who you have on your podcast.
James McKinney: I try to maintain a 50/50 split, yeah.
Minnie Ingersoll: that's fantastic. Yeah, I love it when people say that because sometimes people are like I have this amazing portfolio, its' 30% women. Okay, 30%, you've got 20% more to go. Anyways, so I think there's a lot of that that makes a big difference. At TenOneTen, one of my colleagues is an African American man. He and I would sit on panels together or be at a place together, and we'd speak about what TenOneTen does and afterwards, a line of female entrepreneurs would line up to talk to me, and a line of people of color would line up to talk to him. Even though we have the same check writing authority and the same fund. It's easier to talk to someone who you relate to or look like or feel like has a shared background.
James McKinney: You know, it's interesting, as you were talking I was reminded of an episode that launched just a couple weeks ago with Naysa Mishler from the Everest Effect and one of the things that she said when I posed a similar question is that the idea that you can't be what you can't see, and having that representation there, so that was awesome.
But I'm a believer in honoring the time of our founders and so I want to just have a few more questions for you. When you think of TenOneTen, if we were having a where are they now episode in three years from now, and I'm going to say three years and not five because I know you like to be in the mix and do a lot of things, and so in five it may be vastly different. But when you think of the next two to three years for TenOneTen, what do you want to see the firm accomplish when it comes to the funds that you manage?
Minnie Ingersoll: I do want to carve out the space as the best tech investor in LA. I am sort of competitive about that but what I want to do in a more important way to myself is I want to listen to what entrepreneurs need, and I don't want to like be the best tech investor because I'm beating out other people. I want to understand what are founders needing but not getting right now and I want to be nimble enough that we can be serving the founders that we work w.
James McKinney: As an entrepreneur, I love that so much. It sounds like you want to be the firm that the startups are saying you need to go talk to TenOneTen.
Minnie Ingersoll: Absolutely, because we see a lot of founders who they've rounded up a whole lot of checks but they don't have a lead, so we like to lead deals, but that could change interesting he future.
James McKinney: Oh, absolutely love it. For someone who has such tremendous experience and has seen so many things, and are now on the investment space one of the questions I ask every founder I'm excited to hear your response to it but do you believe anybody can be an entrepreneur or are you born with some genetic makeup that it takes to be an entrepreneur?
Minnie Ingersoll: Both. I think anybody can be an entrepreneur. There's so many different flavors of entrepreneurship and you could be uniquely qualified to be an entrepreneur for a totally different reason than the reason that I'm uniquely qualified to be an entrepreneur. I think leaning in on your strength is super important. That said I don't think everyone would want to be an entrepreneur. It's not, it's like what you're doing here. It's not a glamorous path necessarily so it doesn't mean I think everyone should be but I don't think there's a certain type of entrepreneur that is a type that always succeeds.
James McKinney: I love that. Absolutely love it. One of the questions that I would never cut regardless of how our time was running, it's about gratitude. And the reason I ask this question is I truly believe entrepreneurs need to work in community with other entrepreneurs, they need to be around others. I think the narrative that is propagated out there is this idea of just having your head down and you're isolating yourself and you're just plowing through the solution and the problem, whatever that case may be. And I think that while there may be some case studies that prove that is successful, that's an anomaly not the norm. one of the ways that I believe we can combat this idea of isolate as we're all experiencing now in quarantine, one of the ideas is that we reflect on all the shoulders we stood upon to get to where we are. So when you think back to your journey and all the people contributed to your success and where you are today, who are the people you point to with such immense gratitude?
Minnie Ingersoll: Yeah. I'd start with my mother. I dropped out of Stanford and went back and lived with my mother and nursed me back to health. She's done something like that throughout my life and it's taught me the lesson that I can't do it alone, and I need other people there. I'd also have to point to my husband because I'm able to have a lot of the career that I'm able to have because he has sacrificed his career or he doesn't work right now, and that's enabled me to do a lot of things.
All the people who've done small acts of kindness too. I think I have many people who've touched me in small ways who are not like my official mentor, but it leaves me with a lot of hope that you can do a lot with small acts that have these butterfly wing effects.
James McKinney: I love that. Absolutely love that. This has been an absolute joy to sit with you and for our final question we've been talking to the tens of thousands of listeners at a very high level, just kind of unpacking your journey so that they can see some of the obstacles and the challenges that you've had to work through that they're working through themselves. But right now I'd like to take the conversation from the masses to the one. And my listeners are made up of the frustrated entrepreneur who has been at it for a couple years and maybe cash flow or general traction is a frustration point. Or the want-repreneur, the one who's got a 9 to 5 and a book of dreams and ideas, and some narrative as to whether they believe that the mortgage and they need an income, they can't take this risk, or they think they're 60 and they think they're just too old for this. Or maybe it's the defeated entrepreneur, the one who has tried it time and time again but gets punched in the gut too many times and just about ready to hang their hat up. Whoever it is, I would like to afford this moment to that listener to just have that one on one mentorship from you. What would you say to that person right now as they're sitting in the car or they're running?
Minnie Ingersoll: Probably what I'd say to myself, which is try to think of the thing that you need to do next to move forward with that dream or that plan, or the thing that you've been putting off. What is that next thing? Try to identify that thing and just go do that one next thing, and not try to think about the entirety of all the things you need to do but to think about what's the one thing that would really move my plan forward and see if you can carve out time just to do that one next thing.
James McKinney: Once you've had a few moments to process all the value Minnie brought us in this week's episode, please hit me up in LinkedIn, Facebook or Instagram and share with me your thoughts on this episode. And if you've been around The Startup Story for any length of time, then you know how much emphasis I put on the idea that entrepreneurs support other entrepreneurs. So if you are a startup then there are two very easy ways for you to support Minnie. In fact, it's really supporting you. The first is to engage with her on LinkedIn and we'll include a link to her LinkedIn profile in our show notes. The second, after you connect with her on LinkedIn, is to send her your deck. She's always looking for introductions to great startups that are needing assistance. So let's show up for Minnie Ingersoll and TenOneTen ventures in a huge way as our way of saying thank you to the value she has brought us today on The Startup Story. Remember, entrepreneurs support other entrepreneurs so let's make this happen. And now for my personal ask.
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