Heroes in Business - Jackie Reses, fmr Executive Chairman Square Financial Services, Executive Chair Wish ecommerce site, CEO Luna Financial Group, CoAuthor Self-made Boss

Episode Date: September 14, 2022

Jackie Reses, fmr Executive Chairman Square Financial Services, CEO Luna Financial Group, Executive Chair Wish ecommerce site, Author “Self-made Boss” with coauthor Lauren Weinberg is interviewed by David Cogan host of Heroes Show and founder of Eliances entrepreneur communnity.

Up in the sky, look, it's captivating, it's energizing, it's Eliance's Heroes. Eliance's is the destination for entrepreneurs, investors, CEOs, inventors, leaders, celebrities, and startups, where our heroes in business align. Now, here's your host flying in, David Kogan, founder of Eliance's. That's right. Can you believe it? Another day. I know all of you have been standing by to listen, watching. Well, not so much for me, but really, right? Who I'm interviewing and the amazing things of what people are doing. And you can do it too. And I promise you will always learn something from one of our amazing heroes of how they've got to where they got to, how they made the magic happen and everything.

And by the way, thank you so much for the feedback we continue to have when I had the co-founder of Travelocity on. So make sure that you go to Eliance's dot com. That's E-L-I-A-N-C-E-S dot com why because you know it's the only place where entrepreneurs align all right I'm super excited about our next hero are you ready for this we have with us Jackie Reeses she is the CEO all right the CEO of Post House Capital and former executive chairman of a company you probably have heard of, I know I use it a lot, called Square. You know, the reader Square, as in Square Financial Services. And we're going to talk about her latest book because she is the author of Self Made Boss,

along with the co-author, Laura Weinberg. And you know what? You could reach Jackie by going to selfmadeboss.com. Jackie, amazing. I want to talk about so much stuff. I've read some inserts in regards to your book and everything. But let's first talk about, you know, you're a former executive chairman of Square, like Square Financial Services. Like, I think almost everybody, at least I know, knows Square.

Like, what was, how did you, how did you find this company? Or how did they find you? And how did you get to where you did with them? So I ran a part of Square, and it was truly an extraordinary experience. I was there before the IPO and then through last year when I left to go start a new company related to banking infrastructure. And I think with Square, part of the reason why the company is so special is because Jack and Jim had this brilliant idea around taking mobile payments. And it's even hard to think back to what that was like before you could take a payment with your phone. And they truly are the inventors of that idea. so many innovations subsequent to that associated with Square, whether it's like signing with your finger or the mobile point of sale devices. It truly is an extraordinary company. And so I feel honored to have been a part of it and to have helped build it with Jack. It's a truly great experience because one of the other things that's relevant for your audience is that Square at its heart spoke to small entrepreneurs who struggle with getting their business up and running. And that's frankly why we wrote this book, Self-Made Boss. It's like a love letter

to small business because I think through that experience at Square, I understood how hard it was to get information for small businesses that's super pragmatic to help them start, run, and grow their business. And that's what this book is meant to be. Like, how do you get up and running with true insight that you've learned from other small businesses that you actually can apply that's not theoretical, it's not too high level for any small business to execute on. Well, absolutely. We're going to definitely talk more about the book and how that came to be and some of the things that are in the book of what people will learn. I want to just focus a little

bit more on the Square part. What is amazing, Jackie, as you mentioned, is how come none of these other ginormous companies before Square was even known even did anything about it? Like how did the point come to be with Square of where the idea where they said, one, let's focus on small businesses and doing things that nobody else did? It's really hard to target small businesses because of the economics of targeting that market. You can even look in the banking system, like how do banks support the need for the tiniest customers out there? You'll often find that banks, for example, can only do bank loans of $100,000 and up, but that completely ignores the 30 million small businesses that have less than a million dollars in sales or

the 23 million sole props that are out there that are single person companies. And so I think understanding how to enable people to onboard onto products in a self-serve way makes the economics of doing that very different. And I think the need is so strong for small businesses to get tools that help them build their business, that it's an incredible market if you can figure out how to make those products seamless, elegant, self-serve, such that businesses can find it to be value-add to onboard to them versus like, I don't want to deal with it. It's too complicated to use. You really have to show your value in the first second that you work

with these small business entrepreneurs as a tech product. Otherwise they're not going to have time to deal with you. Everyone just wants to do their craft. They don't want to deal with the nonsense beyond that. And Jackie was Square, and that's Square, as everybody knows, the Square Financial Services, how did you find that position? And I want to then also ask you a little bit more about doing the whole IPO process. So with Square, I happened to know the founder, Jack Dorsey, and I was blessed with multiple years of conversations with him about going to Square. And so, you know, I was very lucky to have had that relationship. And so that's how I ended up at Square.

And then I went before the IPO. And, you know, I think IPOs for a lot of small businesses is often like this dream. But in reality, an IPO is a nice milestone, but it's a financing milestone. And so I think for anyone who aspires to want to take their company public, I hope you aspire to build an incredibly impactful company

and use an IPO as a potential milestone versus something that you see as the penultimate moment for your company along the way. It is a nice milestone for a small business, though, to think like we're going to take our company public. It's going to be amazing. That's huge. And then look, of course, what happened from it going public to just incredible. I mean, everybody uses it and it's really revolutionized. Like you said,

the whole quote access for small businesses to be able to utilize. And it's just, it's been phenomenal. And also too, is you are listening and watching me, David Kogan, host of the alliances hero show. Make sure that you go to

alliances.com. That's E-L-I-A-N-C-E-S.com because we have with us Jackie Reeses. She is the CEO of Post House Capital, also two former executive chairman of Square, as in Square Financial Services. And we're going to talk about her book now because she is the author of Self-Made Boss, along with co-author Lauren Weinberg. It can be reached at selfmadeboss.com. All right, Jackie, why write a book in regards to, first of all, I love the title, Self-Made Boss. Let's get into that. How did you come up with this title of Self-Made Boss? into that. How did you come up with this title of Self-Made Boss? I think it says exactly what entrepreneurs are. I think it's so poetic and perfect for the 30 million people who are putting their heart and soul into being their own boss. It's such a hard thing to do. It takes so much

courage and energy. And I think the title just came to us. And then what we wanted to add to that title, Self-Made Boss, Advice, Hacks, and Lessons from Small Business Owners, is that we are going to be giving true pragmatic experience from small business owners to share with the community. And I think that's an important part of the book because it's written in very pragmatic language. It's written topically so that you could pick it up at any moment in time and look up HR, marketing, ops, onboarding, roadblocks. And so you can go topic by topic. You don't have to read it all at once. It's very approachable and it can just help you at a moment's time to pick out some nugget of experience from some other business owner who also is a small business entrepreneur. And so it's meant to be very useful.

Excellent. And, you know, I think with all of the steps, having started a number of different companies with everything, you know, nobody knows what they're getting into until each of all these things. So it's great that you wrote a book about people who have done it, experience that they've learned from it, and being able to, like you said, utilize those nuggets and that. And with Self-Made Boss, again, you can reach Jackie and get the book, selfmadeboss.com. Jackie, so you mentioned about the nuggets and stuff like that.

Out of the various topics and things that you wrote for small businesses, what surprised you most? And what do you see as, you know, if you were able to pull out one, two, three things from there that is most valuable that people will get out of the book for small businesses? So the thing that surprised me the most happened when I was on a tour of the United States and met with small business owners. And I did this, I spent years traveling around the country and meeting with entrepreneurs. And I was amazed at two things. One, they have genius insights to share. Small business owners understand how to start, run, and grow their companies.

Small business owners understand how to start, run, and grow their companies. The words may sound different than Fortune 500 CEOs, but the insight is equally as smart and unique. And I think that's one of the things we wanted to communicate in this book is the wisdom of those small business owners. And then two, there's lacking a real community. If you're trying to get insight from your peers, there's not a great opportunity to do that. And so we wanted this book to be the start of that community so that you could share wisdom back and forth. are in hiring and around marketing. So let's talk about getting a loan and raising capital. It's really important for small business owners to be able to access capital. They might need it in an emergency. They might need it for ordinary course behavior. If you're really small, the best

thing you could do is go try to find an online lender. And there are ways to do that around a lot of the tech tools that you might use for your business. So Square, Shopify, Toast, Intuit, your accounting software, these are great places where you actually can get financing for your business in a two-click methodology that gives you the opportunity, as I said, in an emergency or ordinary course to get money at a smaller amount than an institutional bank that has a branch might be willing to give you. And so that's a great tool to have in your back pocket. I absolutely would want it in my back pocket, even if I don't use it. You never know when an emergency happens on a Friday night.

pocket, even if I don't use it. You never know when an emergency happens on a Friday night. As it relates to HR, right now, everyone's having staffing problems. It's brutal. And our best advice to folks is to really think about their culture of their company, even if they're a one or two person shop, because the culture often is worn on their sleeve. Meaning if you're a sole prop and you think, I don't need to worry about what my company culture is. It's just me. Well, I don't actually think that's the case. And you should try to think through like, what are you saying to your customers and to the world about who you are? Because I think who you are in terms of how you operate as a business can also get amplified by how you operate with your customers. And having a consistency in that voice can be more impactful in explaining why you're the best at what you do.

Why should your customers choose you? should your customers choose you? And I think it's a consistency in the language and the way that you execute and the way that you go about building your business is all driven from your culture and your principles. And so you could be one person, you could be 10 people. When it comes to staffing, having that consistency as you then grow becomes more and more important. And people want to work for people they're inspired by. They want to work at companies they enjoy. They want to have a good experience. And so if you're able to have thought through that and thought through whether you're providing

a good experience for your employees, super, super important in this kind of market. And then the last bit, I'd say my third bit of wisdom would be around marketing. And on marketing, I would think through the impact of social media marketing and create a schedule. And by schedule, that could mean on Mondays, you show pictures of your customers. On Wednesdays, you show something about how you're an expert at your field of execution. And on Friday, you do some kind of promotion. And I'm not saying use that as the perfect example. I'm saying use it as an illustration of how to mentally put a calendar together so that you can organize yourself and then start to slot in pieces of how you want to go out and produce your marketing. That could be Yelp. It could be Google. It could be next door Instagram. But you should have a consistency to it and almost take the mystery out of that schedule so that you could be a little bit more organized about how you go about doing your social media

marketing. Excellent. Great advice. How did you find the people that you wanted to interview? What was kind of the selection process? How did you know? Because there are millions and millions of small business owners. And Lauren and I went through a process that we called casting. And we called it that because we wanted to include all kinds of entrepreneurs from every state and make sure that we had a breadth of experience represented. And so we had different industries, different locations, different experiences, and then also diversity of background. And so the composite of people who shared their wisdom is excellent. And it ranges from a roofer in Northern California to an oyster farmer in Long Island to a steel company in Florida, to someone who runs an Aspen, Colorado luxury house management company, to a personal trainer in California. We've got it all covered. And I think in addition

to the description I gave, we wanted to make sure that the wisdom that they were sharing, that these entrepreneurs were unique in how they thought through their business challenges. And so it wasn't hard to find amazing entrepreneurs. Now, what's great about the book is that each chapter ends with questions, questions that one should ask and stuff. Share with us maybe some of the maybe more unique or intriguing or questions that someone should be asking? Yeah, well, I think, you know, you want to think through all the dynamics of setting up your business and whether you can establish yourself as an entrepreneur. And so we go through a series of questions about do you have the financing set aside? Do you have the support system you need? And some of that sounds pragmatic and like motherhood and apple pie, except for they're really thoughtful questions that sometimes people skip.

And so as we went chapter by chapter, we almost asked the basics. Like, have you thought about whether your financial statements are organized in a way that you could provide them to an online lending institution or to a bank. And we tried to just keep it very simple so that everyone could say, do I know this? Do I know what happens if I hit a roadblock? And so that's the way we frame those questions. And they're really a synthesis of the content that we've provided in each of the chapters. And how many businesses owners did you interview? Oh, hundreds, actually. We have maybe 40 businesses included in the book. And then we have a series of experts. So the way it's written, each chapter interviews business owners and they tell their story, but they tell it in a way that's a framework.

So the framework was provided by the experts that we also interview. So the example would be interviewing and hiring. And folks who are the heads of HR at very large companies gave us a framework for how to think through that. And then the entrepreneurs filled in the blanks with the story of how their examples might fit into that. It's really, really charming. Now with, again, the amount of people that you had interviewed and stuff, is there a common thread, Jackie? Is there a common thread? Is there like that secret of what you see links all of them are those to be successful? Is that, what do you see having had that experience now of interviewing so many? What's the thread that can make someone successful? successful? I'd boil it down to one word, tenacity. Absolute tenacity. I mean, these entrepreneurs have been up through the ringer, particularly over the last few years. And you see their heart and their soul and they're willing to give it their all,

either because they have to, they feel the pressure because they want to, they've got absolute passion. And the tenacity with which they go and start running, grow their business is extraordinary. And so, you know, we have this funny line in the book that, you know, that goes through like, this is what it takes. And this is what it takes to be a self-made boss. Um, but it's true. It's like, it's the hardest thing in the world to do.

And it's even the part of it around doing your craft is hard enough, let alone all the other stuff you have to do to build your business. And so we truly see that as the underlying thread that ties everybody together. What do you think that either parents and or educators can do for young children who, you know, even start at such a young age of, well, used to be of like delivering newspapers, right? Trying to get their own, you know, street path and everything and that. But for them to be, you know, even if it's a quarter, 10%, as successful as you have been and as smart as you are and the people that you interviewed to be able to be their own, because it is a dream of many, but let's face it, the reality is most aren't able to. So what would you say for either educators or parents of children to educate their kids? Yeah, there are two things. One, I think one of the best things a parent can do is instill

the value of passion and appreciation for what you do. You have to like how you spend your time. And for entrepreneurs, I think that's most important. They need to be passionate about what they're building. Without that, they're going to be miserable. And so I find that they're going to be miserable. And so I find that imbuing that value into kids is super important. And then the second piece of it is a mentality of failure. And you have to be able to fail. And so you got to put yourself out there and then make sure you are willing to pick yourself back up if something doesn't go right and iterate. to pick yourself back up if something doesn't go right and iterate excellent excellent well Jackie this has just been absolutely phenomenal I gotta tell you tenacity being passionate about what you do you're right that's part of the key

you have been part of some of the largest companies and share advice from real small businesses to help them inspire and give others advice. That's a hero. Make sure you reach out to Jackie Reeses. That's right, former executive chairman of Square Financial Services. And you can reach her. He's the author, co-author of selfmadebmade boss calm along with Warren Weinberg all right Jackie with that let's dance away here I have to dance yeah there you go see