305. Identifying Stand-outs at Pre-Seed, Coaching High-Growth Leaders, and Leveling the Playing Field for Underrepresented Founders (Tony Wilkins)

Tony Wilkins of Standing Oaks Venture Partners joins Nick to discuss Identifying Stand-outs at Pre-Seed, Coaching High-Growth Leaders, and Leveling the Playing Field for Underrepresented Founders. In this episode we cover:

  • Walk us through your background and path to VC.
  • Tell us a little more about the thesis at Standing Oaks Venture Partners. 
    • What do you look for in an investment? 
    • What has shaped your framework for thinking about investments the most?
  • What’s the most important thing for an angel investor to know when they start investing?
  • What’s the most important thing for a founder to do when raising money?
    • How do you select for potentially great leaders at the very beginning of their business journey?
    • In what areas do you spend the most time with performing leaders?
  • How do you think about building a strong and healthy culture within a firm? 
  • How does one engineer serendipity?
  • What can VC’s do to support founder’s mental well being? 
  • What are your thoughts on the corporate pronouncements regarding funding underserved founders, especially in the wake of George Floyd? 
    • What will it take to level the playing field for founders? 

Guest Links:

The host of The Full Ratchet is Nick Moran, General Partner of New Stack Ventures, a venture capital firm committed to investing in the exceptions.

To learn more about New Stack Ventures by visiting our Website and LinkedIn and be sure to follow us on Twitter.

Want to keep up to date with The Full Ratchet? Subscribe to our podcast and follow us on LinkedIn and Twitter.

Are you a founder looking for your next investor? Visit our free tool VC-Rank and tell us about your business. We’ll send a list of possible investors right to your email’s InBox!

Transcribed with AI:

Tony Wilkins joins us today from Chicago. Tony is managing partner at Standing Oaks Venture Partners. He has been investing in early stage tech companies for 30 years and coaches executives at growth stage companies. Tony has invested in startups including Cameo, Fetch Rewards and SpotHero amongst many others. Prior to standing Oaks, Tony was in institutional asset management. Tony, welcome to the show!
Thank you very much, sir. Good to be here.
You’re a Chicago legend. I’m sorry it’s taken so long to get you on the show.
Well, I’m a legend in my own mind. And I think my mama might think the same thing. So that’s all accounts.
While I’m very pleased that we finally got a chance to connect but a long time coming. But you know, can you kind of tell us your personal story in your path to becoming a start up investor?
Yeah, you know, people say what, what was your passion in life? What got you here and really, much of what got me here was what I didn’t want to do anymore. I come from a family of six kids in a working class neighborhood on the south side of Chicago, living in that traditional Chicago bungalow that you see all over the city and with six boys, mom, dad and a couple of dogs. My number one objective was to get enough money to not ever have to live in that home again, loved everybody, but did not want to have to come back. So becoming financially sustainable, not a term that I knew back then. And being able to take care of myself was a key driver. In every decision I made from the time I was 13.
So what did that look like in the early days right? Your kid you’re going to school like you know where you work in jobs alongside hustle on your way through or oh man my first job was pulling groceries from the high low. For ladies who lived in the apartment buildings nearby. We pull the groceries in our little rip radio flyer wagons to their apartment buildings. 25 cent customers would have you dropped it off at the front door. The dollar customers Nick, what have you carried it up to the third floor, we fought over those folks. I shoveled snow, I cut grass. I washed windows. I did. Later on we changed oil, we had cars that we changed oil and did minor repair in the garage in the backyard that was at work. So we were always kind of trying to make a couple of extra dollars. And when I got to college, fortunately, I was pretty good attract. So I got a full scholarship to run track at Northwestern. So that took a lot of the heat off of trying to raise money. But nobody told me you weren’t supposed to be an engineering student and an athlete at a Big 10 School same time. So somehow or another I made it out. But I went in any electrical engineering for the sole reason that my dad told me that if you become an electrical engineer, you will always have a job. And, you know, I wasn’t quite sure what electrical engineers did. But dad said you’d always have a job that was good enough for me. And you know, he was right. He was right. I got a great job at Chrysler in Detroit. out of college, you were double E, I was a Double E, that’s right, full on geek and wrote software, did hardware, all that kind of stuff. But I got laid off after the first year. And I realized that job was not what I needed. What I needed was a variety of sources of income that were well diversified that if one went down, the other one could come up. So in addition to buying real estate and moving down to Atlanta to get really involved in investing, I was always keeping my eye out listening to people’s ideas and their stories and see who would want what for me to invest in. And one day a friend of mine told me about investment bankers said those guys, he was involved in a situation where these guys from New York got $9 million for six weeks worth of work and a million dollar bonus. And it was in that moment, Nick. I said I can’t be an engineer anymore. So I’m money space. Money talked loud at that stage. So I moved back to Chicago. Work for AT&T out in Skokie. It was called Teletype Corp. back then. And lived in Evanston, worked in Skokie and went to University Chicago business school at night for three years came out. Nobody hired me as investment banker, but I was very fortunate in that somebody hired me as an as a portfolio manager at an asset management firm, which was my first and wonderful introduction to a group of men who were my kind of like my uncle’s it taught me about asset management, wealth management, taxes, risk horizon diversity, I managed money for high net worth individuals and small corporations, their pension plans for three years. And then I went into sales, selling those asset management services. And that was 88, 89, 90. And then 91, I kind of slap my forehead and I said, Whoa, whoa, whoa, I still have one job. I need to get back to investing. So I wrote my first check with a partner of mine. The two of us were both in our mid 30s. At the time, we wrote for me a pretty big check to fund a tropical fruit beverage company from a guy out of Northwestern, really sharp guy worked at Quaker had this great idea for basically Gatorade for the Hispanic marketplace. And it’s a great idea he had the the product, the formulation, he had the contract packaging, all squared away, we put a lot of money in. Three months later, the contract packager went belly up. And we spent the next year and a half, going around the country trying to get the thing packaged up and wound up not making it. So it’s kind of like football, Nick, first time you get your bell rung. You either take that helmet off, put it to the side and go, you know, tennis sounds nice. Or you say, Oh, that was good. Let’s do it again. So I learned so much in that first loss, that it was really the launch of my I really call that investments called Viva colada averages. If I tribute that first product, that first investment to my the launch of my early stage investing career, so it’s been 30 years, I have learned a ton. I’ve made enough money to stay in it. And I now I think, you know, I might have a trick or two to help other people figure their figure their way around, as I like to say I like to help people shorten their learning curve and avoid avoidable mistakes. So other work in progress.
So yeah, tell us more about what you’re invested in these days. You know, what’s the thesis, so to speak at Standing Oaks.
Yeah, so the thesis at Standing Oaks is pretty simple. It starts off with the premise that in order to make extraordinary returns, you must invest in extraordinary people. So 75% of our investment process starts with the people. And we’ve got we boiled it down to an acronym. The acronym is I see squared, r cubed, I integrity. c squared is chemistry. Coachability. R cubed is resourcefulness, resilience, and responsiveness. And each one of those is kind of a micro test, right? You agree to meet somebody on a zoom call, who wants to talk to you about their business? They show up five minutes late to the zoom call a minute late to the zoom call, Oh, you don’t have my money? How are you going to get back to me when we get going? Or you say, Okay, this is good. Get back to me with your projections for next year. And they get back to you a week and a half later. That’s bad resilience. That’s bad responsiveness. I’m sorry. Yep. Yeah, somebody, Hey, you know what? We’re sales last quarter. Now as a founder, because sometimes in the early stage space, you start off as an investor, but you wind up doing some founder, operator stuff. Somebody says, Oh, yeah, our sales last quarter, we’re about $300,000. About $300,000? I mean, I don’t know about you, Nick. But if I’m an early stage founder, and I’ve worked my way up to $300,000 in a quarter, I know that it’s $287,456. And 40,000 of that was a project that I wasn’t quite sure is going to renew or not. So it’s that level of peeling back the onion of detail of getting to know somebody to say, you know, this is a long and difficult journey that we’re about to embark on together. We’re coming up with an unknown product into an unknown market with unknown competitors sitting in their basements in Cleveland and Culver City, you better be adaptable. You better think of me as a partner down this road. And you really need to kind of look for every bit of help you can along the way and a lot of times people just think they’ve got everything made up they’ve got all the answers. And that’s probably the one thing that will make me run away screaming from somebody if they feel like you know, I know everything that I don’t need, just sit back, give me your money and we’ll talk to you when we go public doesn’t work like that.
Is there a way you tease that out? You know, how do these How do these discussions sort of evolve with you you know, first time you meet an entrepreneur what what sort of questions are you asking to kind of elicit you know, some of that?
Yeah, I want to know what that person And knows they don’t know. I want to know that that person, hey, they may be an expert in whatever it is they do. But if they have any chance of succeeding, they are constantly worried about what Boogie men are under the corners, what baseball bats around down the hall in the dark waiting for him. So I’ll ask questions like this. Hey, who are your competitors? Wrong answer, Nick. nobody’s doing what we’re doing. That’s a bad answer. Hey, do you know so and so? This might be a lady or man who’s in the space and pretty well renowned? Oh, no, I don’t know that person. Okay, it’s okay. You don’t know that person. But you should probably be googling or looking that person up on LinkedIn while we’re talking. Because zoom allows you to multitask. say to somebody, hey, look, my buddy, Nick Moran is really an expert in this space. Can I connect you with him? And maybe have you have a conversation with him? Let him throw some questions at you that I don’t know about. Well, Nick, if I call you back three days later, and that person has not called you that’s not good. Because you have to wake up in the morning and turn over every rock you possibly can to figure things out my favorite founders are the ones who are both able to be still in focus, as well as the ones who can multitask and keep their heads when everything is going crazy.
Tony, is there a certain time that you know you like to enter? Is it a pre seed or seed stage friends and family? Are you more of a series A investor? I mean, you claim some some really great logos? And, you know, assuming you gotten those early, I’m sure you’ve done quite well on them. But I’m curious to stage that Yeah, you typically enter.
Yeah, I can’t afford my pocket book is not deep enough to enter much later than pre seed space. Got it. And I probably am not smart enough to help firm crawl out of that friends and family hole to the light of a real product that is looking for product market fit. So I would say that I am a solid pre seed investor. I like to be the first sophisticated third party investor into a company, I used to invest in a lot of pre revenue businesses, I would say now, it would be very rare that I would invest in a company that hasn’t sold something to somebody not related to them. So grandma bought it. probably not a good signal. But if you’ve gotten somebody to buy your product, or buy it over and over again, wow, let’s talk about what the future might bring so pricy. valuations, certainly under 10 million, preferably under 6 million, very early, maybe the first or second person that the founder is talking to understand, oh, hey, how do I hire people? How do I talk to investors? What is my deck look like? How do I manage the administrivia of hiring people as WTF or 1099? should I? Should I be virtual so that I get an office? What kind of investors should I be looking for? Can you help me figure out how I would support how I would encourage a technical co founder to come on board? Is it equities and stock? What kind of what kind of vesting schedule should I have for my key employees? My partners, my advisers, my investors, should somebody be on the board? What’s my valuation? Those kinds of very early questions that people who have never invested are looking to get some perspective on? I think I do a good job of bringing a lot of perspective and I don’t ever Nick, I learned this from Robin Chata. From the hunter Institute, boy, you got to squeeze. You have to really squeeze hard to get me to give you advice. I don’t do advice unless I have to. I will do perspectives. All day long. Well, you might think about this. You might think about that. Here’s what we’ve done before. I’ve seen this other company do this. I was invested in a company and we did this before. You should go talk to someone so maybe, you know, tell me what you really want to do. So I think I bring questions and perspectives to founders to help them clarify what it is they’re trying to do, and stay focused on where they want to go.
It’s a subtle framing shift, but it’s still important, right? Like, we just saw something really strange come across today. An investor is investing in a safe note one of our companies and he’s asked I want a guaranteed board seat at the series. Round A and I’ve never seen that I’ve just never seen it 35 deals, I’ve never seen somebody try and lock in a board seat for a future round. And so, you know, I didn’t provide advice or anything I just said, this is something I’ve never seen. So I got a call some people to see, like, you know, have they come across this before? You know, I want to call the attorney and get her perspective on this, right? Because it’s just a unique thing. And we need we need those perspectives, right? Like, I didn’t want to jump the gun and say, No, I wanted to kind of understand this person’s perspective and understand how other people have dealt with the situation before.
That’s exactly what it’s all about. Look, I’m, I’ve got kids in my 30s. In their 30s, I got kids in their 30s, I got gray hair. And I remember when I was 20, 25, 30 years old, and looked at people like me, and I didn’t want to hear, I really don’t want to hear what you have to say cuz you’re old. You’re not hip to what’s happening today. So I don’t even know why I’m talking to you. However, I do remember, you know, Uncle Joe, Aunt Bertha, who were older and would sit down and just ask me these penetrating questions innocently and authentically. And make me think, Oh, I hadn’t thought about that. Matter of fact, that is the number one phrase, I look to hear from both coaching clients and investor. founders who I’m thinking about investing in or just people I’m having a conversation with either an office hours at 1871, or Polsky or up the garage? I live. I feel like I’ve done my job when they say, oh, shoot, I hadn’t thought about that. And you can use old people for that all day long, because old people have seen this stuff. That’s right. But I don’t know Tik Tok? I don’t know, Bitcoin, I mean, I understand it. I don’t know a lot of the things that are coming down the pipe that are going to be of interest to the young people who are going to be buying them. So I feel like I don’t have any business, telling you what to do with the time and energy you’re going to deploy to try to make your way in this life. But I can sure ask you some questions that will test whether you really know what you’re talking about, you know, if you’re talking to somebody who has an MBA from the University of Chicago, for instance. And they want to start a company that, in your opinion, is cute and interesting, but not ever going to get them the $195,000 job for the next 10 years that they could get by going to Bain BCG or McKinsey, the question is, pe five years from now are you going to have more money, make more fun, have more, have more money, have more fun and make more impact with this widget business that you’re in. Or by working five or six years, and looking over a bunch of wizard businesses and saving some money in your 401k. And in your regular accounts and stock market to be more well prepared and more well rounded. To do better for you and your family. Then this thing, this really shiny, this shiny object that’s right in front of you that you just put through the new venture challenge. And sometimes people just haven’t done that math. They’re thinking, Oh my gosh, I’m caught up in this and this is exciting, we’re going to go do this thing. And they don’t realize that there’s 77 other people who’ve already gotten funded to do this thing around the country, and I won’t take very long for them to go oops, this was not good.
And sometimes it’s just bright shiny object syndrome. And you know, we’ve we’ve all met some founders out there and I’m probably even guilty of this myself to some degree, Tony. But you know, there’s, there’s lots of fun and intriguing things out there. And it’s, it’s one of the most important things I think every founder needs to needs to remember is just to say no, when you’re doing something interesting, and when you’re bringing a lot to the table and you got a lot of powerful tech. There’s a lot of people that want to work with you and partner with you. And there’s just a lot of potential and you got to get to keep the not the blinders on but you got to keep the focus.
I always say, Nick, people have to know what they want to be when they grow up. Do you want to make an impact? Do you want to be financially sustainable? Do you want to have a holistic life that balances family friends, spirituality impact, cash flow, health, and all those things and many times people Oh, I just thought that was work life balance mine as A lot more to balance than just working life. And, you know, as you go through being a founder, I love the way you put it. There are a lot of shiny objects, and rabbit holes, and it’s okay to look at shiny objects, it’s okay to go down a rabbit hole. But you better have some kind of framework to pull you back out when that thing is not really suiting the objectives that you seriously truly, honestly, individually authentically want to pursue.
So, Tony, on the on the investor side of the table, you’ve been at this, you know, decades longer than I have, you know, what, what, what advice or what important thing would you tell sort of the the new angels or the new early startup investors out there, you know, when they’re, they’re getting their start in this in this industry that, that we’ve all got some scars from?
Yeah, so let me let me go to three basic things. So number one is better to be in a bad business with good people than in a good business with bad people. Because the former will figure some stuff out, they will come up with something to say, Oh, I found this in the trash of the idea that I had before. Bad people. However you decide, however you define bad people will screw will choke the golden goose, trying to get too much out of it. So better to be in a bad business with great people in a great business or bad people. That’s number one. Number two, and this is this is a piece of advice I tried to tell myself to follow but I’m so bad following this one little piece of advice, which is invest in no brainers invest in no brainer. So if you hear if you see something so well, we could do with it. Well, there’s a possible I could see how that would work. Maybe it may be
Yeah, you’re in trouble. You’re going down the wrong path. But I like to tell people, and I hate to name drop, but I don’t think he’ll be mad about this. When I met Steve Galanis of Cameo in office hours at 1871. I was sitting there listening to him. And every sentence that came out of his mouth, I kept going with it. Yeah, that makes sense. That that makes less Wow, that, that’s pretty good. That makes a lot of sense. So I said, Well, you know, go do your thing, keep me posted. And I’m happy to help out with any way I can. But you know, let’s let’s circle back later on. And I kind of lost track of it. Because you know, I talked to about 650 founders a year. And I met with Steve a couple of weeks later, and his traction was off the chart. And the people who he was getting to be getting to use cameo as talent was unbelievable. And his team was so much fun to be with. And you know, I would sit and talk with them. And they would just like be trying to figure out if anything I was saying made any sense to them, you can see occasionally something that makes sense. They write it down, they get after it, I would just like, I love these guys. I love the diverse team that they’ve got. I love the way that they accept everybody’s at least taste everybody’s ideas. And they’re getting traction, what is not to love about this business. And, you know, like anything, you go, wow. If I could always invest in people who I was that interested in that impressed with off the bat, I think I probably would have better returns than the ones that I tried to manhandle into success, because I thought I or we were that smart. And then the last thing I would say is, remember that every investment is going to yield you one of two things, you’re either going to lose everything, and you need to call that tuition. Or you’re going to make some money. And you’re going to call that tax payments, tuition and whatever else is left over. And I think if you think about it as a process that you want to continually get better at, to have fun, help people and make money over the long period of time. You’ll never be really disappointed. I mean, yeah, you’ll be disappointed. But you can always say okay, okay, I learned that lesson that won’t happen again. And it just on the long term, I mean long term like the rest of your life term. This is the one asset that you can get better at as you get older.
You know, you coach many of these CEOs that are further along. I’m curious in what areas do you spend the most time you know, with high performing leaders?
Yeah, there’s three time management delegation and I will call it Culture Management. So we all feel like the more stuff we’re doing, the more we’re getting done. So not true. As you scale from a startup, to an organization where people who you don’t know are hiring people who you’ve never met, to get things done. So I, I start off preaching, hey, delegate, or delete any job from your schedule that only you that somebody that anybody other than you can do anything. I coached a woman who had gone from the executive assistant to the CEO of a healthcare conglomerate, wow. And she was amazing, she could do everything, she could fry up the break and bacon and bring it home and cook it up and go at a board meeting and all these things. It’s like, you need to chill. Hire an executive assistant, don’t ever make another airplane reservation, don’t ever schedule another meeting. And you live in Naperville come to work in an Uber or in a limo or on the train every day. Get back those hours, that your shareholders need you to be doing high volume high quality work for. And you could look at the look on your face like, yeah, I guess I don’t need to spend an hour back and forth with Hilton trying to make sure they’ve got their reservation bar night. So letting go of the stuff that you’re comfortable doing is important. Carrying the culture, curating the culture, I think culture is not good or bad. It’s how we do it here. And I came across a great term the other day from a woman who said that they they preach cultural humility, meaning, hey, this is exactly how we do it. This is the way we run it, how we treat people how we treat our customers. Don’t ask us why we do it this way. This is just the way it happens. That’s, that’s a strong culture. And the CEO should make sure that some stories and off sites and examples and emails and the way they reward and punish people, that culture is reinforced. But they need to be humble about it, and say, Hey, if you’ve got a better way of doing this, bring it and encourage an environment at the shop so that the last person through the door feels just as comfortable making a suggestion appropriately in the channels that have been laid out as the person who came in that started that business with you. Because you need every possible advantage, you can get to move forward. And everybody has to feel that way. We also talk about and this is another one straight out if you give the Huntsville Institute credit on this one, I think Brian Burkhart was when it came up with it, which is as you scale, you must lower your expectations and raise your standards. So if you and I start a company together, we thought about it, we’ve had a few drinks, we had dinner, and we’re like, Let’s go, and I know what to expect from you. And you know what to expect from me, we’re gonna have to write down we’re trying to figure this, but by the time we hire the 17th person in our shop, they don’t really have all that background, they may have just got laid off of Northern trust or someplace. And they’re just looking for a place to work. There has to be some pretty strong guidelines about what this job entails, how we do what we do and what our mission is. And as you scale those standards has become more important. So I’m constantly begging founders to document the standards. Because as my mother would say, you have to pray for the best, but prepare for the worst. So the best would be you hire somebody who was referred to you by a longtime friend of yours, they come in and oh my gosh, this is the greatest job for them. And they get along with everybody, and they’re adding so much value to the company. That’s wonderful. Let’s pay that person a lot of money and celebrate them every time. However, in a startup, you can’t always hire the people, you need to hire the people who will come work for you.
Often, those people will not be with you for long. And you must have a fair and transparent way of coming to the conclusion that this is not a good mix for either one of you, which means performance expectations, which means co created objective expectation or expectations and standards. Here’s how many widgets you’re going to make every day. Here’s what time you come in the office. Here’s what time you leave. Here’s how long sick time and vacation and all this stuff all laid out because it could come to pass more often than not, it used to have to part ways. Now if it’s just the Nick and Tony show, and our annual recurring revenues, you know, $4,000. And we say, hey, Alex, you’re just not working, you got to go. We can get away with that. Because a $4,000 a month, there’s no attorney that’s going to say, let’s go and sue them for wrongful termination. But if we have $400,000, of monthly revenue, and we say, Alex, you’re paying the behind, get out here, don’t come back. Oh, Lord, somebody is going to show up and say, did you have a process? Was this discriminatory? Was there a hostile work environment? Was this person fairly evaluated? Did you did you discriminate because this then the other, and we’re probably going to go You know what, you know what, let’s just settle and be done with this. And just the distraction and the financial drag on improperly documenting things like personnel strategies, is just poor corporate hygiene, when in fact, this is the kind of thing that I think I do for early stage companies. Like hire a PEO. Call somebody from trying to or engage Pro, or Insperity and have an employee handbook and make sure that everybody reads it, and have periodic reviews and make sure that you’re deducting the right stuff for people who live in Iowa part time and live in Chicago part time and you’re part time, let that PEO professional employment organization handle all that so you can still focused on the business. So managing your time carrying the culture and standardizing the business are the probably the three strings on my guitar.
What can a coach or or an investor for that matter do to support founders mental well being this is a challenging, challenging, especially the single founders out there. I mean, they have to deal with an enormous amount of pressure and stress across many different areas of the business sometimes for many years, right on ahead. And so you know, any any thoughts or perspectives on that, Tony?
Yeah, I’m gonna I’m gonna name a couple of names of people who I know are really helpful and useful in this and I don’t know the folks that headspace. But, you know, I said before, it’s not work life balance is life balance. So if you are not eating properly, sleeping properly, getting away from time to time, disengaging from time to time, as an investor, I don’t need you to be wearing yourself out. routine maintenance is good for cars, for houses, for boats, for relationships, and for individuals. That love and that kind of routine maintenance, the most important I mean, the physical part of your bodies is important. But psychologically and I’m you know, it’s good that we have people who are paying more attention to this, there’s a company in Chicago called stigma, which is working to help reduce the stigma of asking for Ariana Gibson. Yeah, there you go. There you go. I love that love that company. Ryan Monday, as a company called alchemy health, which is for black people who traditionally don’t reach out for help to have a personal way to kind of get themselves calm down and move forward. And there’s a lady in Chicago named Gina Murata, who is just a goddess in the mental wellness space in terms of providing perspective, and ways to think more holistically about how you move your life forward. I always ask you, what do you want to be when you grow up? best answer I ever heard that very happy. Very happy. And happiness needs to be attended to with the same care or even more than your financial projections. Because that’s just one aspect of
I love it. I it doesn’t get enough air time. And usually it’s too late, you know, and if you let it go too long without giving it proper attention, but yeah, you know, and the funny thing is, Tony, maybe you’ve seen this over the years, but you know, you see those founders that they’re going through the war of like trying to find product market fit, and you can tell like their hair is a little disheveled and they’re they’re closer, disheveled, then like they find product market fit, they get the next funding round. And you know, the hairs all trimmed up and nicer. And like, it looks like they’re actually getting sleep. And it’s just, it’s amazing, the different phases that people go through to try and make these these companies work.
Yeah, well, you know, you can’t put out a fire with an empty bucket and got to refill yourself. Every now and then I have a funny story. There was a founder in Chicago and Nick, trust me you have mixed emotions, trying to tell your founders to slow down. Yeah, because if they’re rolling, and they’re Write in and things are happening. And you know that they’re sending you emails at 2:30 in the morning, and then they got a six o’clock call, you’re like, yeah, I want you to do that. I want you to make hay while the sun shines, but are you doing it sustainably and occasionally, I think it’s important for investors, particularly at the stage that I operate at, to just come in and swoop in and take your investor, take your founders out, we hit this one young lady who was just phenomenal. She’s She’s working on a billion dollar company right now I’m tickled that I got a chance to invest with her. Very, very early on, I got a call from her co founder who said, Hey, so and so I’m not going to mention her name, because she’ll be embarrassed is sleeping. She’s sleeping underneath the boardroom desk every night. hasn’t been home in a week, and won’t take any time off. No, kid. I said, I’m glad you caught me with this information. I got this. So again, this is one of the benefits of being a very early stage investor. You know, these folks, often before they’ve sold their first thing, often before me, I get a chance to hear them say a lot. early on. I hadn’t thought of that. I hadn’t thought of that. I hadn’t thought of that. By the time they get to be Seed, Series A is more vertical specific. And I’m not that guy. But I called her up. I said, Are you at the office? Yeah, yeah, of course. I’m at the office. Okay. All right. Well, I’m coming to the office at four o’clock, I’m going to pick you up. We’re going to drive to Union Pier, there was another founder, another investor in Union Pier, we’re going to Joe’s house, we’re going to walk on the beach for an hour. And I will bring you back. After we have fed you and you can start working again. It’s 7:30. Okay, but I got to meet, cancel a meeting, push it off, let somebody else take it. I’ll be out in front and half an hour. And I picked her up. Her co founder was there I think give him your phone. She thought I told her to cut off your left arm, give him your phone. So she was phoneless internet lis. We laughed and joked and drove out to Union Pier. We found the founder if on the other investor, we walked up and down comparitech or shoes off, walked up and down the beach for about a half an hour, 45 minutes, got something to eat, filled her stomach up, we had some traffic on the way back, she fell asleep and started snoring. And by the time we got her back to the office, she had been in such a deep sleep. She’s like, Where are we? And it was just I mean, four and a half hours to take her out, calm her down and recharge. Now she’s an amazing entrepreneur, four and a half hours was plenty for her. But it’s our job as investors to look out for the total package of the people with whom we’ve entrusted our money and who have entrusted us with helping to guide them to where their lives are going to be very big. And at my stage of the game, it’s usually not the first rodeo these people are going to be at and the lessons that they learn hopefully, off the off the backs of the painful memories that I’ve had to live through, will help them get there faster. And with more fun.
Well, many of these folks that we work with, they can run so hard and fast for so long. It’s it’s really about shifting direction slightly and making sure there’s a little bit of balance, you know, they don’t need a push, they just need a little bit of a, you know, pump the brakes every once in a while.
That reminds me of a term that one of my buddies from Kentucky used to tell me about when he’s talking about hiring people. And I use it also in terms of investing people say, you know, far better to settle a racehorse than to have to kick a mule. And you find a founder that you got to kick over and over again, probably need to either start to write that thing off or don’t write that check in the first place. But yes, in Chicago, we got a lot of race horses really work and and you know, it’s a privilege to be able to be around and guide them either as an investor and advisor, or just somebody that they meet in office hours every now and then.
Tony, I want to talk for a minute about underrepresented founders, maybe a place to start, you know, what do you think of these corporate pronouncements regarding funding and underserved founders, especially in the wake of George Floyd?
I am thrilled but you know, Show me the money. There are a couple I will call a Google Founders Fund. This is the second year in a row that they’ve put $5 million worth of undiluted financing into founders, of course, I think they’ve got their fingers crossed that those founders will use a lot of Google products when they get done. But that makes sense to me as a gamble shareholder. Yeah, let’s do that. And then Wellington Capital Management, my good friend, Danny sharp, and now Van Jones, who’s running the investments in black founders in the United States, focusing on direct investments and fund of funds. I mean, if you say you’re Gonna put a billion dollars. I’ll also say also that Morgan Stanley is doing a great job and has, I think they’re on their 15 to 20, a fund of their minority innovation system in New York. And I know that get the name wrong, Carla Harris will call me up and tell me I screwed that up. But there are a number of organizations, I met a guy today I just was introduced to a guy on LinkedIn who’s heading up Deloitte minority initiative, there are corporations that are saying, hey, this makes sense, this is the right thing to do. Let’s figure out how we can all move forward together, and they’re writing checks, and they’re hiring the right people to put them in the right places to do what makes sense. And quite honestly, screen through the noise that they wouldn’t even know is noise, to get money to people who are going to have an economic return, all for it, call me anytime happy to help and lend my shoulder that on the other hand, this is just the way it is sometimes there’s some people who are going to jump in and try to make noise to say, Oh, yeah, I’m cool, too. I’m all in as well. And then you go, I thought, I thought you said you were going to put $1.5 billion to work, I haven’t seen 1.5 dollars yet. Now, there may still be working on it. But it’s been a year and a half. So I think we all have to, as we do in life, pitch in with the people who are actually doing some stuff. And just ignore the folks that aren’t until they decide they’re going to fix it up. But I think the longer term situation here is going to be that under appreciated talent will eventually as it always has in the United States, be recognized, honored and compensated. Can you imagine? Can you imagine a country where there were no female legislators? Well, that was United States before 1920. And that’s so unbelievable. for somebody to think about it. Can you think of any major league sport that does not have black athletes in it, it’s incomprehensible. So we will get there. In the business environment, when we see a number of I mean, availability bias helps, too, you see a couple of companies that are led by men or women of color. And you go, Whoa, whoa, whoa, okay, so I don’t want to be left behind. When this train goes through, and the fact there are people like me, probably a little bit younger, who are looking for diverse talent, because either they have more access to them, or they have better relationships with them, those dollars are going to start to trickle into. So I look, I’m probably the most optimistic person on the planet, I don’t need a glass to be half full. I just need to be wet. So I’m very bullish on it. And I tell founders all the time, I said, Look, I don’t like gravity. And I didn’t like school. But it’s a fact of it’s a law. And it’s something we all got to go through and passage of time, I’m convinced will will level the playing field. We all need to be doing what we can to make that time come a little bit faster.
Well, in light of some of the call outs you had I want to give a quick shout out to Project33. And actually, Ariana Gibson’s sister, Deseret Vargas Wrigley who’s writing checks. I think they’re 25k, 50k checks like every couple weeks, every few weeks, right? And long jump capital is Long Jump, Long Jump’s another one. So we’re starting, we’re starting some initiatives to kind of help push the needle here and get to do more on that front in Chicago and beyond. Yep, I think it’s kind of Tony, if we can feature anyone on the show. Who do you think we should interview and what topic would you like to hear them speak about.
Oh, man, I would love to have you get Sam Yagan on the show. And talk to him talk to Sam about his galactic ability to multitask. As a board member of a startup and CEO of a publicly held company, I get a chance to spend four hours in a car with Sam one time coming back from a wedding in Wisconsin when he missed his flight. I just felt like I was in the car with a legend. And Sam is just off the charts smart, humble, helpful, successful, just a fabulous person.
Tony, what do you know, you need to get better at?
Saying no. I come from a family where our motto is a Wilkins man can fix anything but the crack of dawn and or broken heart and we’re working on both of those two right now. Well, you know, it’s probably not worth our time to be thinking about fixing the crack of dawn and broken hearts. Who knows why, but I know I have a hard time letting go of a promising entrepreneur who’s really trying to get something going. And although I’m much much better at saying no, I’m not interested in this right now. Cuz I don’t want to drag people on, if I do sense even a glimmer that there’s something there because I live in the very early stage space, I got to see things that haven’t manifest themselves yet, I got to get better at telling people. This is not of interest to me, I will keep you in mind in case I find somebody for whom this investment makes more sense. That’s what I’m working on every day.
And Tony, finally, what’s the best way for listeners to connect with you and follow along with Standing Oaks?
On the standing ups website, if it’s a founder, who is interested in having a look at investing in their company, all of our criteria is there. And then there’s a button that says if you still want to talk, give me your name, address and five sentence five word description of the business five sentence description of the business and I will get I’ll get back to you or somebody else will get back to you. If it is somebody who’s saying, Well, you know, Tony, you said something that really made sense to me. I do use LinkedIn as kind of my first contact with people. So if they if they say, Hey, I heard you, I just don’t respond to people who say they want to connect. But if they said, Hey, I heard you on Nick Moran show and what you said on new stack about blah, blah, blah is important. Can I spend five minutes 15 minutes with you talk about it? I’m probably gonna say yes, and send them my Calendly we’ll have a 15 minute conversation.
Very good. Well, the man is Tony Wilkins, the firm is Standing Oaks. He is a legend in the Chicago Community. But I’d encourage founders anywhere to to check out the website and reach out Tony, thank you so much for for all the wise words today and in all the perspectives, really appreciate it and can’t wait for the next one.
My pleasure. Thank you for having me on and putting up with me for an hour.
Thank you, sir.

Transcribed by https://otter.ai