Can you make your business feel “effortless”?

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 Storyarb 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 Now on to the episode. What's up, everyone? This is Alex Lieberman, and Founders Journal is back, baby. It has been 8 months since I hit publish, and I'm feeling more energized than ever to share what I am learning as I am building businesses and talking to some of the smartest business builders in the world. For those of you who are longtime Founders Journal listeners, welcome back. Thank you as always for your ears and your trust. For those who are new to the show, the show, here's the deal. I created Founders Journal during the pandemic as a way for me to document the entrepreneurial journey. It was my audio diary of sorts to share my experiences while I was in the arena, and also for me to memorialize my career in a way that I could listen back 50 years from now. The mission today is no different. I want to help increase your odds of success as a business builder by sharing the stories, lessons, and emotions that I experience as I am building my business. You can expect the podcast two days per week, Monday and Wednesday, with episodes that are intentionally bite-sized under twenty minutes. And if you want to get notified when a new episode comes out, make sure to subscribe wherever you're listening to the show. Now let's hop into episode one of Founders Journal Rebooted. Over the last few weeks, I've been heads down on 2 of my businesses, StoryArc, which is my content marketing agency for high-growth B2B companies, and CTA, my media agency helping B2B companies scale creators and new media channels. One business feels like an absolute rocket ship right now. The other feels like we are running in quicksand. And this dichotomy between the two has made me appreciate that building a business is this never-ending game of things feeling effortless and effortful. It is inevitable that you will feel both of these things as you build a company, and the time horizon can vary from hours in a day that swap from effortless to effortful all the way to full months or years that feel like they are more of one than the other. And since this duality in entrepreneurship feels unavoidable, a sort of law of physics in startups, the thing that I am always thinking about is when things feel effortless, how do we keep things there as long as possible? And when things feel effortful, how can I guide the business back to effortlessness as quickly as possible? I want to focus this episode on the latter question because I think it's probably the more common feeling in startups, and it is the most important to understand how to navigate. If things feel effortful, how do I get them back to effortless as quickly as possible? And to answer this question, or really any question with complexity in business, my brain always goes to creating a simple concept that I can easily visualize and that allows me to break down a problem into its component parts. So what I want you to do is I want you to imagine a ship. It can be any type of ship. I just ask that it has sails, a crew. So the analogy works. I'm going to imagine a pirate ship just because I'm a child, and that feels like the most fun. So I imagine that I'm the captain of a pirate ship. I have my steering wheel. I assume that pirate ships have steering wheels. I have my sails, my crew. I have the wind at my back. I have the waters out at sea, and I have a buried treasure that is hidden on a beautiful island far away. I know this sounds absolutely ridiculous, but it's all going to make sense in a minute. And I'll actually use examples from my businesses to help understand how I move things from effortful to effortless using this analogy. While I've never been a pirate, nor have I captained a pirate ship, I can imagine that there are 2 general states out on the seas. One state is a state of ease where the ship is gliding through the water. The wind is at our backs. The sails are drafting off the wind perfectly. The crew is killer and working in unison. The water is calm and the boat is pointed just as it should to be able to get to the treasure quickly. Most periods in a business are not this state, but when you have it, you know it. And when you don't, you are fighting like hell to get it back. The other state is a state of effort. The ship feels like it can't advance any slower. Maybe the wind has changed direction and is hitting us head on. Maybe the boat isn't pointed in a way to benefit from the wind. Maybe one of my crew members is sleeping on the job. Maybe the waters get choppy. Maybe the boat has holes and is taking on water. You're starting to see where I'm going with this. These 2 states with your ship are the 2 states that you experience as an entrepreneur. Your boat is the product. Your crew is the team. The wind is your market. The waters are your customers. The sails are your marketing. And the treasure is your long-term vision. Now, here is the process I go through with any of my businesses. I first orient myself to how things feel aboard the ship right now. Am I in a state of ease or a state of effort? If you're not sure, the answer is probably a state of effort. The longer you build businesses, the faster you can identify which state you're in. Again, for the sake of this episode, we're going to assume we're in a state of effort because I think it's more important to figure out how to problem solve this. Then the next question becomes, what is leading to this effort? What are my bottlenecks that are causing my ship to move slowly and sluggishly? I generally think that the parts of the pirate ship that you are able to control are the best types of bottlenecks. Adjusting your sales or your marketing strategy is the easiest. Replacing the wrong people isn't easy, but it's within your control. The same thing with where your boat is pointed. A change in strategy or vision is painful, but it's within your control. And fixing your boat, the product, takes a lot of time. But if you have the right people to change it with you, it is not life or death for your business. The things outside of your control are the wind and the water. The wind, which again is your market, is the most important factor that determines success with your business. But you cannot control it. If you get your market wrong, you're not dead. But it goes back to your people. You need to feel exceptional about your ability and your team's ability to read the wind and know when you need to change direction, fix your boat, and swap out your people if you've gotten the market wrong. That is why picking the wrong market is so painful, because adjusting for being wrong for it can involve wholesale changes to all of the things that are within your control on your ship. New boat, new people, adjusted sails, new direction. So these are all of the possible bottlenecks your ship can face. And it is your job as the founder to understand which bottlenecks are the root cause of your ship not moving smoothly. This is where you try to take in as much information as you can and diagnose what are the root causes. And depending on the root cause, that will inform just how drastic the adjustments you make need to be to move back to a state of ease. And the final step is once you know which one or several parts of your ship or the voyage are causing effort, then it is about prioritizing adjustments to get back to ease as quickly as possible. So now that the analogy has been played out, let me use an example of one of my businesses, StoryArb, to take you through this analogy and our journey. I started StoryArb 2 years ago. For the first 3 months, here's what things looked like. My pirate ship was made out of cardboard and tape. I was the captain and the crewmate, and I was trying to row as I steered the ship. The Treasure was becoming the go-to partner to help founders and executives build their brand on social media, and it felt like hurricane-speed winds were at my back. Demand for what I was offering was insane. Every founder I spoke with wanted to build their brand on social media but did not have the time or the skill set to make it happen. So as the wind was at our backs and the boat was gliding through the water, my priorities were twofold: improve the ship so that it didn't disintegrate while trying to get to the treasure, and finding people so that I wasn't steering and also rowing the boat. I improved the ship by hiring copywriters to handle the writing, which they could do way better than I ever could. And I ultimately brought on a co-founder as my first mate so they could start managing the crew on deck and I could help steer the ship from above. But then something happened. Crosscurrents picked up on the water. They were strong and basically negated all of the wind that we had at our back. I started to worry that no matter how hard the crew paddled, no matter how much I adjusted the sails, no matter how much the boat was improved with process and people, the boat would never get to the treasure. We had a customer issue. Initial demand for our product was strong, but retention was horrible. After 4 to 6 months of working with a founder, they would send us an email saying, we need to talk. And every conversation went the same way. They would say that they learned a ton from us. They saw the value of building an audience online, but one of 3 things wasn't working for them. First, they didn't have the time to show up for interviews so that we could get content from them. Basically, they were too busy and other priorities had picked up in their business. Second, they didn't feel like the voice of our copywriter, even though it was good, it didn't feel like it was the same as their voice, and that was uncomfortable for them. Or third, they didn't feel like business results were happening fast enough, so they didn't think that creating content online was worth their time. We very quickly realized we had a big frickin problem. Our product was wrong for the market we were in, and that was causing customers to churn, which meant we could either change market, change customer, or change product, or multiple of these options. We needed a new boat, one that could cut through the crosscurrent, or we needed a new customer so the crosscurrent would go away, or We needed to reposition the boat in a new market with a new treasure. So in the context of StoryArb, a new boat would have looked like serving the founder's desire for personal brand support differently, in a way that we didn't have to worry about retention past 6 months. And I think the products that were best positioned to do this would have been something like high-dollar-priced personal brand workshops within Fortune 500 companies, or maybe an online personal brand course for founders that customers could expense to their company card, and they would take the course once and they would use the knowledge from that for them to create content online after. And while I think that this was a new boat that could have gotten to the treasure, the reality is it would have involved completely changing my crew, basically wholesale firing and rebuilding of the boat and removal of the crew. And my co-founder and I weren't willing to do that. Another option was to change customer instead of selling to early-stage founders, which was our initial customer for StoryArb. We could sell to communications or PR teams who support later-stage founders. Now, this wasn't a horrible option. We'd be switching the customer from viewing our product as a nice-to-have to viewing it as a need-to-have, given it is a PR person's job to create a megaphone for the business. But our fear with this option was a fewfold. We didn't necessarily have access to later-stage companies at the time. And even though our customer changed from founder to comms person, at the end of the day, the founder could still be the bottleneck to us succeeding since we relied on them, which then led to us asking ourselves the question, how can we reposition the boat and the crew that we have to be pushed by a growing market and not hindered by the crosscurrents of low-retention customers? And the way we tried to figure out which way the wind was blowing was by talking to our customers constantly and also talking to our teammates who were on the front lines of our business talking to customers every day. And what we heard was the following: our clients, who are mostly B2B companies, have tons of content needs outside of just executive social. They know that content can drive leads for their business, but they don't have marketing resources internally to do all of the things that they want to. And so this insight intrigued us. We could tell that there was this tailwind coming from B2B businesses looking for great content that drives demand. Now we had to figure out how different our boat and crew had to be to get back to a state of ease. And to get to that answer, we just had to keep asking our customers questions to inform what the new product would have to look like. We asked them, what content formats do you care most about? What are the biggest problems you're facing as a marketing org? Who is owning the content strategy for you today? And ultimately, we got to a place where we had clarity around what we needed to do next. The boat definitely needed upgrades. We had to go from focusing on executive social for founders to creating a what I call connected content motion that included playbooks, editorial newsletters, and socials now for heads of marketing instead of founders of companies. The good part about all of this is that our crew really didn't need to change all that much to push forward. What did need to change was our boat. It needed a complete overhaul, which meant things were going to get painful for a 2 to 3 month period. We would be moving forward while taking on water. Pailing out the water, patching holes, and just continuing to go full steam ahead. But what I am happy to share is today the pirate ship at StoryArc is moving full steam ahead with total ease. And I think that one of the reasons is because my co-founder and I were able to use this way of thinking about a business to evaluate all of the component parts, identify the root causes, and make changes we needed to get back on course and see a clear path to the treasure. So that is it for the first Founders Journal episode back. Thank you so much for listening. As always, I am so energized to be back and doing what I love, which is storytelling the entrepreneurial journey and sharing my lessons, my emotions, and the stories along the way. 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