Becoming a multipreneur

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 and this is Founders Journal. For those who are longtime Founders Journal listeners, welcome back. For those who are new to the show, here's the deal. Founders Journal is my audio diary made public for the world. My goal is to increase your odds of success as an entrepreneur by sharing the stories, lessons, and tactics I experience as I build my businesses. You can expect the podcast Monday and Wednesday with episodes that are under 20 minutes in length. And if you want to get notified when a new episode comes out, make sure to subscribe wherever you listen. Today on the pod, I am talking about being a multi-preneur, what it means, why I'm doing it, the risks associated, and lessons that I have learned along the way. Now let's get into it. Let's start by setting some context. After stepping out of the CEO role at Morning Brew in 2021, I was lost. My motivation went from a 12 out of 10 to a 2 out of 10. I wasn't sure who I was outside of Morning Brew. I had no clarity on what I wanted to do post-exit, but all I knew was that I couldn't sit around all day feeling crappy and I needed to figure out what was next for me. One of the most valuable exercises I did was something called the Best Stuff, which is an exercise that has you identify and describe eight specific accomplishments or experiences across your entire life to understand your zone of genius. From that exercise, a few things became clear: I have three gifts: invention, storytelling, and curiosity. And as I reflected on these gifts, when I used them most and when I felt most energized building Morning Brew. Everything pointed to the early days of the business. From 2015 to 2019, when Morning Brew had less than 20 people and under $10 million in revenue, and the business was defined by firsts—first newsletter, first sales pitch, first hire, first office—I was the happiest guy in the world. Post-2019, when Morning Brew was scaling from 20 to 300 people and $10 million to $70 million in revenue. I lost my love for the game. Building the business felt more like science than art. Product building was replaced by organization building, and my gifts felt less valuable than ever before. That led me to asking myself a simple prompt: How can I design my career in a way that honors my gifts and preserves what I felt in the early days of Morning Brew? Getting to this answer was a nonlinear journey, but where I netted out was what Greg Eisenberg calls multipreneurship. Here's how he describes it. A multipreneur is someone who creates multiple products per year with the aim of creating a company that creates companies. For 20 years, we've had venture studios or product studios. Their entire shtick: pump out venture-backed startups like a factory assembly line. But we're not in Kansas anymore, folks. This is 2023. Creating a product doesn't require you to cozy up to VCs looking to bankroll your ideas. You don't need a Scrooge McDuck-sized vault of cash to get your dream off the ground. And let's throw out the old rulebook while we're at it. No more go big or go home. No more bending over backward to raise venture capital in the it places. Who needs geographical validation when you can get community validation? That's where the real juice is. Everything else, just noise. Forget what the big shots say. Listen to your community. They're the ones who matter. Everything else, just static on the airwaves. That's exactly why I've been championing the concept of community-based products for such a long time. I'm advocating for a shift away from traditional venture capital towards a new model I call Venture Community. It's about turning to your community for validation and growth, not just the deep pockets of venture capitalists. With this freedom, you can make multiple bets per year, stay creator-led, operate with low overhead, and integrate each of your products together. Let's put some clarity on the board here. A multipreneur isn't just a beefed-up solopreneur. Trying to juggle 5+ businesses solo is like playing dodgeball with a dozen balls coming at you simultaneously. It is a spectacular failure waiting to happen. Imagine the first time the customer service inbox lights up like a Christmas tree. Boom, you're toast. So let's not confuse these terms. Being a multipreneur is about building small, capable teams for each venture, fine-tuning your game as you progress. It's not about going at it alone. It's about leading a pack. Most importantly, AI, no-code, and global talent allow you to be a multipreneur from anywhere in the world, giving you the Freedom to work wherever you want, whenever you want, with whoever you want, faster than you ever thought possible. So that's what being a multipreneur looks like, and I love Greg's definition. Now let me talk about what that's looked like in practice for me the last two years, the biggest risks with this model, and the most important lessons that I have learned along the way. My high-level plan with being a multipreneur has always been to build a portfolio of businesses that I am the co-founder of all of and the CEO of none of, which allows. Me to spend the majority of my time in my zone of genius. More specifically, that means my business process generally follows the following playbook. First, I find an idea either through my own discovery or brought to me by someone else. Second, I help to incubate the idea, which means testing demand, creating an MVP, bringing on and servicing initial customers. Then number 3, I try to cash flow the business as quickly as possible, finding and bringing on a co-founder and CEO as soon as the business can afford Number 4, I set a very clear expectation with that CEO around my model, and that expectation includes my goal is to increase the odds of success of this business and decrease the time to scale it significantly, that my plan is to spend 20 to 40 hours a week on the business in the early days and then ultimately scale down to a few hours per week once it reaches stage 2, which is when it goes to company building from product building. And finally, that my goal is to fire myself from the business within 12 months and be the executive chairman. And then the 5th part of the process is to work hand in hand with my co-founder to get the business to product-market fit and have a strong core team so that me stepping out of the day-to-day of the business is not at all disruptive for them. 2 years since building this plan, I have finally seen it executed successfully with one business, which is StoryYard. Here's the quick timeline. 2 years ago, I had an idea to help founders with their personal brand on Twitter and LinkedIn. I got my first few customers quickly. I started servicing them myself, and then I brought on my co-founder Abby, actually originally as a consulting CEO to start just 2 months later. Once the business could afford her, it took us around 16 months, one small pivot and one big pivot to get to product-market fit. And today, Abby is fully running the business. She has a full-time team of 18. The business is on a $3 million run rate and accelerating. It is highly profitable, and I am spending 2 to 3 hours on the business per week on average. So experiment number one with being a multi-preneur is a success. But there are tons of lessons and risks that I think about constantly. So let's go through them one by one. First, Picking the right CEO is everything. You can only have leverage and build a portfolio of businesses if you trust your partners to execute autonomously and successfully. Buffett can only run Berkshire fully as a capital allocator because he has GMs and CEOs of all of his businesses and business units that he trusts implicitly. Now, one big difference between me and Buffett, other than literally everything is a difference, is that I not only have to worry about picking the wrong CEO, I also have to worry about if a CEO will be able to run multiple types of businesses, because one big risk of me bringing on a co-founder and CEO as soon as we can afford them is that the business may not truly have product-market fit yet and we may have to pivot. This is exactly what happened with StoryArb, and thankfully Abby was able to run the business when it was both an executive ghostwriting agency as well as now a content marketing partner for B2B companies. The second lesson: everything takes longer than you think. I learned this at Morning Brew with having a slide in our initial investor deck in 2016 that shared a 1-year plan, and it actually took 8 years to get to. But I have relearned the lesson with StoryArc. While my original goal was to fire myself from the business within 12 months, in reality it took 18 to 20 months to get there. What I've been asking myself recently is what to make of the difference in timeline. Was 12 months not realistic? Did I not pivot fast enough? Should things look different with future businesses now that I've been through the whole process once? I think it's a little bit of all 3. I do think we were pretty quick with pivoting StoryArb when we knew that the original business was going to be too high of churn to make it attractive long term. I also think as I build more businesses, I will be able to spot patterns faster and not have to wait nearly as long to know whether something is working or not working, which is a perfect segue into lesson 3. Pivoting is the rule, not the exception. Morning Brew spoiled me. Our original newsletter is almost the exact same as the newsletter that people get in their inboxes today. Yes, the design has improved. Yes, the writing is a hell of a lot better than Austin and mine. Yes, the website actually functions. But for the most part, Morning Brew had product-market fit since day one. So I assumed this was the norm. Now that I have built StoryYard and I'm working on a number of other projects in my portfolio, I'm realizing I was wrong. The odds you nail the first product from the jump of your business is almost 0% because you just don't have enough information yet to know exactly what your customer needs. Which to me means that your ability to take in information, distill signal from noise, and know when the right time is to shift course is one of the most underrated skills of an entrepreneur. Pivoting is a superpower, not a negative thing, despite how it is perceived publicly. Lesson number 4: You need the right structure when being a multipreneur or you'll succumb to time suck. I have 7 projects, including StoryArb, going on right now. And while there's an argument to be made that it's not as crazy as it sounds because most of these projects are at a very early stage, which means some percentage of them will never become real businesses, It is still probably too much. By definition, the timeless risk of multipreneurship is doing the exact opposite of what most successful founders say is the key to success, which is focus. And although I think there are ways to be focused as a multipreneur, it is very easy to get unfocused very fast. And one of the ways to do so is by saying yes to too many ideas. So in this next phase of my multipreneur journey, a huge to-do for me is to create more rigor around the following questions. One, how many ideas can I work on at any given time? 2, what is my process for qualifying ideas? And 3, what are the milestones I need to hit to continue to requalify ideas into legit businesses? Lesson 5: As a multipreneur, you need to think of yourself as a product and your customer is your co-founder. The only way for me to be able to maintain significant upside in businesses that I launch while being able to step out of the day-to-day is to offer so much value to my co-founders and CEOs that it is worth their time. And if I can't do that, then either I don't get meaningful upside, I don't attract the right talent, which keeps me in the weeds of my businesses too long, or I don't have the ability to fire myself after 12 months, which also breaks the entire model. So how I think about it is simple. What do I need to offer to increase the odds of a business's success by multiples? And what do I need to do to speed up the time to real scale by multiples as well? For me, it's 3 things. First, distribution. Having a trusted audience gives me and my businesses unfair access to customers, employees, feedback, ideas, and potential partners. Second, my zone of genius. My 3 gifts— invention, storytelling, and curiosity— significantly increase the odds of getting through the 0-to-1 phase, which is the riskiest stage of business. And 3, my network. Past the 0 to 1, my network of founders, investors, and operators gives my co-founders and CEOs access to resources and information they wouldn't otherwise have. That is the product I offer today, but it's obviously something I plan to refine and make even more compelling as time goes on. The last lesson, lesson number 6, multipreneurship is not for everyone. Multipreneurship shouldn't be an empty goal. It should be the solution to a problem you're facing. My problem was that I love the zero-to-one of business. I found it the most energizing. I found my skills most conducive to it, and I wanted a way to focus most of my time on it. That's why I wanted to be a multipreneur. I'm doing this while acknowledging that the risk of being unfocused is something that I'll need to be obsessed about fighting as long as I build in this way. But if you're not trying to solve for a specific problem that multipreneurship offers you, then it very likely may not be worth the trade-offs that are associated with it. That is it for today's Founder's Journal. Shoot me an email to alex@storyarb.com. That is alex@storyarb.com. Say hi, hola, what's up, or whatever else takes you less than 10 seconds, and I will get the conversation going. I love getting to know my listeners so that I can make this show as valuable as humanly possible for you. Thanks again for listening to Founders Journal, and I'll catch you next episode.