Founder Mt. Rushmore

What's up, everyone? This is Alex, the host of Founders Journal. As you may know, I built Morning Brew from my senior year of college until we sold the business in 2020. And now I'm building a variety of businesses in different spaces and different stages. I'm basically averaging 1 to 2 new businesses per year. And because of that, I have had the opportunity to test a ton of different products and services, ultimately landing on a core software stack that serves as my business operating system whenever I start a new company. I have my go-to banking service. I have my go-to formation service. I have my go-to domain hosting service. But probably the most important of them all is my HR service, Gusto. If you're a longtime Founders Journal listener, you know how much I think about people in the context of business. A business is nothing without its people, which means a platform that helps me manage and take care of my people is invaluable. And that means I've tried every HR platform under the sun, always with the same exact goals in mind. First, I want a product that's intuitive and delightful to use. As a non-HR person, I find the intricacies of payroll, benefits, taxes, compliance, and expenses to be painful. So I just want something that makes my life easier. Second, I want it to be affordable. I'm a bootstrapper at heart. I started Morning Brew with $0 and I started StoryArc with $0 as well, which means I don't have infinite dollars to drop on SaaS products. And third, I want a platform that acts as my one-stop shop for all things people. I want it to handle payroll, benefits, hiring, onboarding, and taxes, all while integrating with all of the other tools in my business stack, whether it be QuickBooks, Slack, or Google Workspace. Well, Gusto hit the trifecta, which is why I am a customer and use it for every single one of my businesses. Yes, this is a paid sponsorship by the amazing team at Gusto, but I would sing their praises even if I wasn't being paid to do so. So if you're looking for a platform that takes the pain out of payroll, benefits, and HR, I highly recommend you check out Gusto. And if you sign up at gusto.com/alex, you will get your first 3 months free. Now onto the episode. What's up everyone?

This is Alex Lieberman, the host of Founders Journal. And today on the show, I am talking about how my heroes in entrepreneurship have evolved over the last 10 years. Let's hop into it. So this episode is a reflection of a conversation I just had with the founder or co-founder and CEO Of gusto, Josh Reeves, and you're going to hear the celeb shot Founders Journal that he did with me over the next few days or weeks. But I just want to share kind of my thoughts on our conversation. The TLDR is Josh is like a top three entrepreneur that I've spoken to in the last ten years. Everything that he's about and embodies is what I hope to. Kind of emulate in my career as an entrepreneur. He is well-valued. He's deeply aligned to the mission of his business. He's built an incredibly large company. He's wildly ambitious. He's built a now famous culture within Gusto. Gusto has one of the best cultures in Silicon Valley. He's a family man. When he's not working on building his company, he's spending time with his wife and his kids. And it was just so refreshing to kind of hear from what I consider to be the full package in entrepreneurship. And it gives me hope that you can kind of have it all as you build companies. So what I want to share is how my— let's call it Mount Rushmore of entrepreneurs has evolved over time and why my Mount Rushmore looks a lot like Josh Reeves. So when I started to build Morning Brew, you know, at the end of college and after graduation, I had kind of the cliché heroes in business— Elon Musk, Jeff Bezos, who else? Mark Zuckerberg, for sure. Bill Gates. And, you know, I— when I ask myself why, why were these people my heroes, it's because I viewed their journey as entrepreneurs to kind of be the thing that I wanted to do. They ideated their business from a garage or from a classroom. They built the thing and then they grew the thing and ran it through IPO, right? All these businesses these entrepreneurs worked on for 20-plus years, and they went literally from the negative 1 to 1, all the way from 1 to 1,000, and built, you know, generational businesses. But then as I was building Morning Brew, something started to become clear to me.

Yeah.

A lot of these entrepreneurs and just honestly, a lot of entrepreneurs that I came across didn't necessarily fill all of the cups that I wanted to fill in entrepreneurship. You know, I started realizing that a lot of founders that I knew who were, quote unquote, really successful were people who only spent their time on work. They were in their 40s or 50s. They either were single, divorced, didn't have families. their companies became their deepest relationships. And, you know, this episode isn't for me to pass judgment on those founders. It's more about me having self-awareness of what I want in my life and then trying to match that to people who can kind of almost act as Sherpas with kind of in a dark cave with the flashlight on pointing me in the right direction. And so, you know, as I was building Morning Brew, it became clear to me that, you know, these unbelievable entrepreneurs like, you know, Gates, Musk, Bezos, yes, they're incredible builders, but for the other cups in life, like family, spending time with your children, they weren't necessarily the models that I wanted to emulate. And I think, you know, there's a few reasons that it became clear to me that my original Mount Rushmore wasn't gonna be my final Mount Rushmore. One piece was just like, As I steeped myself more and more in entrepreneurship and company building, it became clear that so many founders around me prioritized their companies and their professional life over their personal life. But the other piece that happened was like my life evolved and I entered new chapters in life. So when I first started building Morning Brew, right, I was a college student. I graduated, I was single, I didn't have kids, I didn't own a home, I wasn't married. And so There weren't really any other obligations in life or things that I cared deeply about other than the work that I did. But then, you know, as I got married to my wife, as we started thinking about having a family, all of these things, it became clear to me that in the next chapter of life, like, I had one North Star. And that North Star was I wanted to prove to myself that it was possible to be an A+ entrepreneur and be an A+ family man. And if I couldn't do both of those, then I wouldn't consider myself a success kind of in my own eyes, because sure, if I built a multibillion-dollar company, but it was done at the expense of being a great husband and a great parent, then to me it wasn't worth it. And I think part of, you know, this desire to kind of have it all or fill both of those cups, one just comes from the way in which my parents raised me. Like the, the thing that my dad and my mom always said to me is, Family is first, family above all else. But then losing my dad when I was a junior in college just reiterated to me the fact that the time you have on this earth is limited and the time that you spend with your partner and with your kids is also limited. And so you really need to be intentional about the way that you spend your time. Otherwise, your life will fly by and you'll live with regrets of not having spent it in the way that you want to. And so anyway, all this to say, you know, as I got to the later years of Morning Brew, it just became clear to me that this Mount Rushmore had to change. And as I think about who are the people that sit on this Mount Rushmore, to me, it's the people that, that really represent the North Star that I'm trying to build towards. People who are great family men, great fathers, great, you know, community people and also are great builders. And so to bring it back to, you know, Josh Reeves, I'm really excited for you guys to listen to the conversation with him. But to me, he, he represents it all. He started Gusto when he was— I think it was 2010. It was 2010. So, you know, he's building— been building the thing for 15 years. It's a $10 billion-plus company. It's a company that serves 400,000 small businesses, helping them with kind of all of their HR needs from payroll to employee hiring, onboarding, insurance, all of these things. And just to make it clear, like Gusto is a sponsor of this show, but I literally said to my wife after talking to Josh that I will be a customer of Gusto's for life because of what Josh represents to me. You know, he has built a great business, but he's built a great business what I consider— and there's no right reasons, but what I consider to be the right reasons in my own eyes, which is he's Deeply aligned with the values and the mission. He cares so deeply of building a great organization and being surrounded by smart and good people. You know, the culture of the company is amazing. You're going to end up hearing in the episode that he did. Like, he has so many great traditions that show how much he cares about people. The one story I'll quickly share is that in the early days of Gusto, when it was just a small team, when they hired someone. And they were calling the candidate to tell them that they were going to give the person the job instead of it just being the one hiring manager calling the candidate. The entire team, the entire Gusto organization, which at the time I presume was a small team, would get on a speakerphone and call the candidate and they would all congratulate the candidate and they'd go around and each person would share one reason that they were so excited about hiring this person. And even though Gusto has 2,500 employees today, the company still does the same thing. Obviously, not all 2,500 people are calling every new employee, but it's every kind of hiring team, right? Because when you go through a hiring process, multiple people interview a candidate. Everyone who did an interview is on the call to welcome the candidate and say why they're so excited for them to join the company. And so to me, just Josh represents everything that is great about entrepreneurship and also having it all. He's well-valued. He values family as much as he values business because he values family. That hasn't at all stifled his ambition. He's built a $10 billion-plus company. And so, you know, I just think about moving forward. The entire way that I'm structuring my life is one that hopefully is not going to decrease my level of ambition at all. Right? Like, I'm working on 4 companies right now. I think several of them can literally be billion-dollar companies, but I'm not willing to make the trade-off of building billion-dollar companies if it means that I am not able to be the partner and the parent that I want to be. And so all that to say that I think as you as an entrepreneur think about what your North Star is, and by the way, like I said, there's no one right North Star. Mine is to be an A+ family man and A+ Entrepreneur, yours could look totally different. But what I am saying is I think it is really valuable for you to build kind of your Mount Rushmore of entrepreneurs and make sure those entrepreneurs kind of are anywhere between one to five innings ahead of you. So you start feeling like you have a path to follow, a playbook to follow to reach your North Star. And for me, that looks like people like Josh Reeves. It looks like people like Kevin. Kevin, who was the founder of MongoDB and Zola and Business Insider. He is an amazing entrepreneur at all. For whatever reason, his last name is escaping me right now. But again, someone who's incredibly well valued as a family man and businessman. And my hope in kind of building my life towards this North Star, and this is why I continue to create content on the internet, is like in the same way that that these entrepreneurs are kind of acting as the guides for me to reach my North Star. Me creating content online is going to hopefully provide a playbook for the next entrepreneur that wants to live— I'm not going to say a balanced life, but a life that is full in the way they want it to be full. And so that is how I think about the evolution of my Mount Rushmore of entrepreneurs. It's how I think about Josh Reeves, the co-founder and CEO of Gusto, being added up Onto my new Mount Rushmore, and it's kind of my ask of you to be unwavering in your North Star. Know that it is possible to have it all, but knowing that you need kind of the right guides and the right playbook in order to reach the endpoint you want to get to. As always, thank you so much for listening to Founders Journal. Shoot me an email if you want to introduce yourself or ask me any questions: alex@storyarb.com, and I'll catch you next episode.