If at first you don’t succeed
Friends,
When I was a kid, starting a company was no big deal. It’s snowing outside and people need their driveway cleared. So grab some buddies and a few shovels, go door to door, and figure out what people will pay the cute kids from down the street to shovel (pathway to the house and sidewalk included of course).
Lemonade stand, why not. Old Pokémon cards, sure you can take them off my hands… at the right price.
In fairness these aren’t capital “C” Companies per se. They’re more like side hustles for a kid with no allowance who wants to spend time with his friends making some cash for 7–11 slushies. But in the age of venture capital and rocketships, the idea that at its core, a business is selling something for money that people want, can sometimes get lost in the noise.
I’ve spent the better part of the last year trying to build a startup of my own from the ground up. No venture studio to provide expertise and guidance every step of the way. No angel investors to provide external validation and clout along with a steady paycheck to take the edge off the journey. My goal was to bootstrap through Series A and takeoff from there. Ambitious? For sure. Naïve? Perhaps.
In 2021 I realized that I could use the wellness wheel as a framework to categorize areas of satisfaction in my life. By the end of last summer every dimension was at or near all time highs. Physically I was in the best shape of my life. Spiritually I was more connected than ever. Socially & Emotionally my morning Tefillin & Mussar meditation practice was going strong, I had friends and family all around, and I had just married the woman of my dreams. Intellectually I discovered the power of podcasts and audiobooks for endless learning, Environmentally I was loving NYC, and Financially I was in the position to take multiple years off from working without having to forgo any of my life’s daily comforts.
The time felt perfect to take a leap of faith, follow my creative urges, and pursue a mission of my own making. With all other seven dimensions of my wellness wheel in place, I could take a risk Occupationally to build a startup that was truly me and also made the world a better place. I was at the top of my game, ready to conquer the world.
Well, all that didn’t last long.
Want to practice the virtue of humility? Try building a startup.
A buddy of mine told me that his startup experience aligned with a quote from another Elon in town — that building a startup is like chewing glass. There were many days, and a number of weeks, where I certainly felt that to be true.
The two ideas I was working on were actually designed to help people with different aspects of their wellness wheel. The first idea, “Kinly Concierge”, was a social wellness platform aimed at helping men optimize for the relationships in their life. Afterall, less than half of men are satisfied with their friendships. The second idea, “Pocket Guru”, was designed to help people connect to a spirituality that is truly their own. Religious dogma is falling out of favor with many Americans, yet the number of people identifying as spiritual, but not religious is growing at a steady clip. Without a safe space for spiritual inklings to be nurtured, many seekers are choosing to shut down the spirituality of life, making them less resilient, more isolated, and more depressed in the process.
Both of these pain points resonated with me deeply, giving me the energy needed to set off on the journey. And I did make some good initial progress. Kinly had multiple pilot customers paying hundreds of dollars a month, while Pocket Guru had nearly a hundred beta users, a fully built AI-backend, and a marketing plan spearheaded by an Emmy-Award winning producer & NYTimes best selling author.
Yet I found both businesses to have holes. Kinly was predicated on building a network of social concierges, but with ChatGPT’s public launch in December, it became clear that a scalable business for personal assistant type work would need an AI underpinning. Pocket Guru had AI at its core, but D2C app building is grueling, and without a clear path to deep user retention and monetization the road ahead felt overwhelmingly long.
It’s funny how the wellness wheel can hit a negative spiral just as fast as it can hit a positive one. Perhaps both Kinly and Pocket Guru could have succeeded if I kept trying, but I found that worse than trying to solve the business problems at hand, was trying to manage my energy levels, which day after day, week after week, were draining. My workouts and diet got worse. My financial runway felt a lot shorter than it initially seemed. Occupationally, I started questioning if I was even on the right path. And emotionally, I was using meaningful effort to keep up a positive disposition that typically comes to me naturally. Thankfully the nature of the businesses I was building forced me to keep my social and spiritual wellness strong, and a regular cycle of reflecting, meditating, and journaling let me keep things somewhat level and in perspective.
Ultimately though, you know what I say to building a startup is like chewing glass? F$$$ that.
Building a startup should be fun. You should be surrounded by people you like, working on a mission you care about. You should be enjoying working hard because you’re solving interesting problems and creating something new in the world that wouldn’t have been there if you weren’t around. You should be being pushed forward by people who make you want to strive to be your best and do your best work. You should be generating value for customers and getting paid for that value creation. Most importantly, you should feel energized by the work you’re doing and the people around you. Will building a startup be stressful at times? Of course. But short term startup stress does not need to go hand and hand with daily anxiety.
My entrepreneurship journey over the last 8 months was definitely more glass chewing than fun. And so I burned out. I knew before I left my last job that if the time came I’d be able to get another job. Yet there were a handful of times over the last year when I doubted that reality. It’s with gratitude and a smirk at the moments where I did have doubts, that I can say I have landed firmly on my feet. Better yet, everything that I had been hoping for when I started my solo-startup journey has actually fallen into place.
I couldn’t be more excited to share that I’ve joined the founding team of Chariot, a NYC based fintech company on a mission to get more dollars into the hands of nonprofits via its Donor Advised Fund payment solution. The mission is powerful and taps into a hyper growth market segment in philanthropy. The team is great with individual areas of excellence that compound when collected as a unit. And the daily, fast-paced, in person culture is exactly the type I love. The financial backing of some amazing VCs and the killer team lets me focus on growing at what I do best — defining clear GTM strategies and finding win<>win solutions for customers and partners alike.
And best of all, I’m having a ton of fun.
Being back to having a full time job that’s fun and energizing does something else too — it lets me get back in the positive reinforcement cycle of my wellness wheel, creating mental and emotional space to focus on the things I care about in life. It also means I have more energy to work on new passion projects in my free time, even though my overall amount of free time has gone way down.
With the experience of the last year behind me, I can now look to the future with a reorientation for how I want to approach these passion projects. Rather than planning for my side hustle to turn into a rocketship startup ASAP, I can go back to the company building of my youth — spending quality time with my friends doing something that I love — coming up with fun ideas that solve an immediate need while delivering real value to the people we’re serving. I can also more deeply appreciate that life is short, and I should continue to optimize for spending time doing the things I love with the people I love. And if something I’m doing doesn’t fit that criteria, I’m blessed to be able to say no just as fast as I say yes.
The adventure continues,
Elon
P.S. In using the wellness wheel both personally and as a framework with friends, I’ve found that when one dimension is off life feels stressful. When 2 or 3 dimensions are off, life can feel completely off the rails. In these stressful times its easy to get tunnel vision on the dimensions of trouble and ignore the other parts of the wheel — but I’ve found that particularly in these moments, assessing all 8 dimensions can put things in proper perspective, making the stress feel a lot more manageable. Putting some effort into a non troubled dimension also creates a healthy outlet for regaining confidence and positive energy that can then be used to go back to addressing the dimensions of struggle.
P.P.S. If you’re interested in some of my personal takeaways from the last eight months, here’s a list of my top 5.
- External accountability is big: I would say I am generally a highly motivated person. But when there’s no one seeing when you wake up in the morning, how many hours you worked this week, or if you hit your goals or not, it’s just too easy to miss deadlines and procrastinate. I tried using a coach and an accountability buddy with limited success. There’s just nothing like a boss, teammate, or direct report counting on you to make sure you get your work done well and on time. Are you annoyed when you’re forced to work when you don’t feel like it? Sure. Do you feel great once you’re finished, knowing that you actually got the work you needed to get done, done? Most definitely.
- I need to be around people: I’m unquestionably an extrovert. So spending a week in my apartment working on a solo project is just about the worst working environment I can have. Being able to go to my brother’s startup office 2x/wk and the techstars nyc office 1x/wk did wonders for me. But still, there’s a big difference between working around people vs. working with people. Teammates who are invested and are working towards the same goal as you is a big amplifier to the working together feeling.
- Faith in good times is nice. Faith in bad times is impressive: There’s a saying adopted from the teachings of the Lubavitcher Rebbe: “There is only good news. Either it’s obviously good, or it’s good that’s yet to be revealed”. It’s a philosophy that helps reframe any situation so that you can find, or at the very least build towards, the positive. It rests in the belief that ultimately God has a plan and everything will work out as it should. Meditating on this idea, particularly in the moments when things feel like they’re actively not working out as they should (as far as you think they should that is), is where the real muscle of faith is built. That faith is solidified when you get out the other side and everything does in fact turn out to be alright. And for those of you asking — if you haven’t found the good yet, then you haven’t reached the other side yet. Keep going :)
- Journal on a computer: I tried journaling with pen and paper a handful of times, but the issue is my handwriting is sloppy, my spelling stinks, and I’m a slow writer. Once I started stream of consciousness journaling on my computer, I unlocked the power of getting all my thoughts down ‘on paper’ and the relief that went along with it. I found that similar to Jack Kornfield’s teaching — the repetitive thought patterns of my top 10 tunes were taking up a lot more space than I realized.
- Starting from zero is a muscle totally unique to itself: I think the biggest takeaway of my journey is this: I love to create. As the great Zava says: “When you put your passion in life, life puts its passion back in you”. The feeling of chasing an idea and trying to build it into existence, is a thrill I love. By taking the last year to focus exclusively on launching projects of my own, I’ve flexed the muscles of starting new projects completely from zero — muscles critically important but hard to actively work in the world of fulltime employment. Now that I’ve gotten in a few reps of shipping a prototype and getting people to use a solution early, it’s a lot less daunting to do it again for new ideas as they arise.
If you read this far I appreciate you. I hope my sharing this made some kind of positive impact on your day. And if we’re long overdue for a catchup please don’t hesitate to reach out! Sincerely, Elon.
