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What I’ve Learned In My First Year as a Solopreneur
8 min read

What I’ve Learned In My First Year as a Solopreneur

What I’ve Learned In My First Year as a Solopreneur

Exactly a year ago, I announced that I was leaving the world of institutional venture capital to pursue a career as a coach, advisor, and angel investor. I honestly had no clue what the path was going to look like or where it would lead me. This was one of the most difficult decisions in my life. It was very much a leap of faith.

Here’s what I knew: I wanted to spend half my time coaching and the other half working on creative projects and investing as an angel. I also knew that I badly wanted to work for myself. The idea of getting a job didn’t appeal to me. I was 0 for 3 at venture firms. I always felt like a fish out of water. Given this, I was finally ready to bet on myself and step into my power as a solopreneur and coach.

Transitioning from VC to coach and creator has forced me out of my comfort zone. I’ve had to adopt new mindsets/perspectives and also shed old ones that were no longer relevant and useful. I’ve also had to acquire new knowledge and skills to support my business and the founders I serve. I’ve had to stretch in more ways than I expected.

Given my first year as a solopreneur has come to an end, it’s an ideal time to step back, reflect on what I’ve learned and share some of those lessons with you. Here are the most important things I’ve learned this year.

1. Bet On Yourself.

There’s tremendous power and freedom in being a solopreneur. At the end of each day, I’ve either moved the business forward or I haven’t. I don’t have anyone to blame or point fingers at. It’s all on my shoulders. I’m the creator. I’m the owner. This responsibility is empowering and motivating. Over the past year, I’ve pushed myself to accomplish more than I ever have while also maintaining strong work/life balance. I started High Output, raised an angel fund, launched The Founder Library, and redesigned schlaf.me. I’ve come to realize that all of us are far more capable and powerful than we often believe. We just need to give ourselves permission to step into our full power. I wish I had bet on myself sooner.

2. Find A Calling.

There’s a big difference between having a job, a career and a calling. Institutional VC felt like a career to me. While I enjoyed it at times, it drained me more often than not. Coaching feels like a calling. It fills me up every single day. I now get to focus almost exclusively on the part of investing that I loved: serving the entrepreneur and building deep relationships with them. I wake up every morning fired up and ready to get to work. I’m not exaggerating. I truly love what I do. I don’t view this as a three year job. I’m committed to helping thousands of founders while also achieving mastery. This is a multi-decade journey.

3. Follow A Mission.

During the first week on my own, I carved out a few days to draft a personal mission statement. I had never done this before. I reasoned that it would help me sharpen my focus and direct my full energy towards a cause. My essence of my mission is to help founders bring their boldest visions to life and evolve into extraordinary leaders. While that will likely change over time, everything I do right now maps to that mission. It’s a forcing function. I’ve begun to appreciate that there are countless paths towards this single mission. The fun part has been identifying and deciding which ones to take.

4. Ask for Help.

Early in my career, I struggled to ask for help. I viewed it as a sign of weakness. It’s nearly impossible to create anything great in a vacuum. I learned this the hard way. Once I became a solopreneur, I made a personal commitment to ask for help, leverage my network, and collaborate with friends. I encouraged myself to ask for advice, favors, and intros even if I was uncomfortable. I had to put my ego aside. I’m glad I did because I’ve received support from countless collaborators who have pushed my thinking and opened up new doors. This includes family, friends, coaches, founders, investors and even my Twitter followers. I wouldn’t be where I am today without support from others.

5. Invest in Mind, Body & Spirit.

Beginning in early 2020, I made a serious commitment to double down on my health. I wasn’t working out consistently, getting enough sleep, and eating well. I had unconsciously picked up some bad habits. I needed to get my act together especially if I was going to build a business and perform at a high level. Since early this year, I’ve deepened my daily meditation practice, worked with a virtual trainer, adopted intermittent fasting, studied under a Buddhist teacher, slept for 7-8 hours consistently, cut down on sugar and processed foods, and achieved five years of sobriety. The results speak for themselves. I’ve lost twenty pounds and my output has dramatically increased. I’m now able to show up with more energy, intention and awareness for those I serve. I’ve never felt and performed better in my life.

6. Protect Time For Deep Work.

When I was a full-time VC, my days were typically filled with back to back to back meetings from 8am to 6pm. I wasn’t able to get very much accomplished creatively. I could tell this was having a material impact on my output so I made time for deep work a priority. For the first time in my career, I began to protect my calendar in the morning. I made a commitment to reserve 8:00-11am for blogging, journaling, and any critical/creative work (read: not email). This one change has been a massive unlock. It provides me with time and space to get the most important tasks accomplished in the morning when I have the highest capacity to do great work. I can’t recommend this enough.

7. Automate The Business.

As a solopreneur, there’s not enough time each day to accomplish everything on my list. For most of this year, I’ve relied upon a variety of manual and non-optimized business processes. This included a patchwork of software applications and templates that don’t talk to each other. Just a few months ago, I began to realize that I was dropping the ball and spending too much time outside my zone of genius. I’ve slowly begun to automate and streamline some of my core administrative tasks. I wish I had invested the time and energy into this sooner. Automation is going to be a major focus in 2021. I know it will provide tremendous leverage and unlock even more headspace.

8. Define Your Box.

Let me fill you in on a secret. I’ve suffered from ADD all my life. As a result, I’ve struggled with saying no, standing still, and remaining focused for prolonged periods of time. I would often chase after every new opportunity without giving it much thought. Over the summer, I hired Chris Sparks, a performance coach, to help me get focused and begin to prioritize the endless stream of opportunities flying at me. With his support, I defined a set of filters and constraints to help me decide what I focus on and where I spend my time. In other words, we defined what fits into my box. Through this process, I’ve come to appreciate that constraints are my friend. They help me get to the heart of what’s most important and essential. As a result, I’ve been able to dramatically increase my output and go further faster.

9. Give Yourself Away.

When I first started coaching, I let my clients decide how much they paid me for my sessions. I valued helping others and getting reps over monetizing my time. During the height of COVID in the spring, I coached dozens of founders and leaders in crisis for free. When we were creating The Founder Library, we decided to make it a free community resource. When I blog in public, I share my secrets and hard earned lessons for free. What’s my point? Providing value without expecting anything in return has been a huge accelerator for my development and career as a coach and creator. While I don’t know or care how this will come back to me, I believe the universe will somehow reward the positive that I put out into the world. I’m already seeing this in action. Karma is powerful.

10. Ignore Sunk Costs.

Few people know this. I spent two months working on a podcast called Big City Dreams. I produced eight episodes with some of the most diverse and fascinating entrepreneurs in New York City. I had a website. I had a trailer. I had a marquee sponsor. I even had a blog post ready to announce the project. So why did I press pause right as we were about to launch? The project wasn’t filling me up. It was stressing me out more than it was energizing me. After hours of introspection, I decided Big City Dreams wasn’t the right podcast for me to host and produce. Given the size of the time commitment, I set aside the sunk costs and focused on the future costs. I reasoned the future costs would far outweigh what I had already invested. This allowed me to refocus my energy and eventually create The Founder Library.

11. Meet People Where They Are.

This has been a difficult year for millions. Clients have been fired, shut down their companies, executed mass layoffs, struggled with mental health issues, lost family members and much more. Every single one of us is dealing with our own challenges and adversity. It’s nearly impossible to know exactly what someone is experiencing. That's just one reason why expectations can be very dangerous. My good friend Jonathan Basker couldn’t have said this any better: “It’s not about you. It’s about them. Honor where they are in their own journey.” This advice hit me hard. This perspective has helped me honor and meet those I’m serving exactly where they are.

12. Consider The Power Of Context.

Humans are complex organisms. Our perspective of the world is colored by our experiences, culture, knowledge, needs, values, environment, and more. Additionally, every organization is unique. They have different employees, customers, products, partners, processes, systems, and competitors. In other words, context matters a lot. It’s critical. As I’ve gone deeper into coaching, I’ve come to appreciate that taking a “one size fits all” approach doesn’t work especially in a highly complex world. This learning has helped me take a systems approach to coaching and support each client as a whole individual. Context is more important than content.

13. Run Experiments.

Three years ago, I ran a workshop called One Change Club. I spent more than six weeks designing and planning the workshop in a vacuum. I didn’t get any feedback until the event was over. What a huge mistake. Since then, I’ve realized there’s tremendous power and leverage in running experiments, prototyping, shortening feedback cycles, and shipping sooner than you want to. Instead of launching an eight week coaching fundamentals course, I hosted an AMA with aspiring coaches. Instead of launching The Founder Library as a stand alone site, we created a Notion page as the MVP. Here’s my point: find the essence of what you’re trying to accomplish, do that as quickly as you can, learn from it, and iterate. This has been a huge unlock for me.

14. Enjoy The Path To 10,000 Hours.

I spent the last decade of my life learning the venture business. I’ve now dedicated the next phase of my career to mastering the craft of coaching. I’m somewhere between 1,000-2,000 hours on this journey. I view every session, conversation, YouTube video, podcast, and book as an opportunity to learn, grow and strengthen my practice. I’m putting in the work and getting the reps. I’m taking it one day at a time. Brick by boring brick. I’ve come to understand and appreciate the process and dedication required to become a world-class coach. There are no shortcuts to 10,000 hours. I’m enjoying every second of it.

To Infinity And Beyond!

The past year has exceeded all of my expectations. Making the transition from full-time investor to coach and creator hasn’t been easy but it has been insanely rewarding and fulfilling. Every day is stretching me in new ways.

I’m finally living life on my own terms and doing exactly what I want. I’m fully aligned with my mission and values. I have boundless energy and creativity. I’m exactly where I should be.

So what’s next? I have no clue yet where 2021 will take me but I know this: I’m more excited for the future than ever before. There’s endless territory to explore. I see opportunity everywhere I look. The sky's the limit.

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