Henry Dotson's Blog https://henrydotsons.blog/ en Sat, 22 Aug 2026 05:48:53 -0700 Flying Solo https://henrydotsons.blog/2026/08/22/flying-solo.html Sat, 22 Aug 2026 05:48:53 -0700 http://dotsoniv.micro.blog/2026/08/22/flying-solo.html <p>Hi. I&rsquo;m Henry. I started my journey in entrepreneurship in 2014. Since then, I&rsquo;ve had the opportunity to work with remarkable people on meaningful projects. Here is a quick timeline:</p> <ul> <li> <p>2014-2016: the startup years. Started two companies with teams. Both failed. Learned 200 things not to do.</p> </li> <li> <p>2016-2020: the real estate years. Started an Airbnb company with a friend. Sold it in 2020 to move on to the next thing.</p> </li> <li> <p>2020-2024: the writing and research years. Worked for a few big startups, wrote biographies billionaires and bootstrappers, explored the world of communities and masterminds. The most lessons and insights.</p> </li> <li> <p>2024-2026: the client years. Worked one-on-one with founders as contributor, consultant, and advisor. Mainly equity partnerships and retainers. Seeking PMF, and sometimes finding it. Mainly trying to prevent the same early mistakes I made from sinking ships.</p> </li> </ul> <p>Now, I&rsquo;m building my own things. I&rsquo;ve always worked with teams. Turning a new leaf and working on putting out into the world the things I dream.</p> <p>Stay tuned for more.</p> Hi. I'm Henry. I started my journey in entrepreneurship in 2014. Since then, I've had the opportunity to work with remarkable people on meaningful projects. Here is a quick timeline: - 2014-2016: the startup years. Started two companies with teams. Both failed. Learned 200 things not to do. - 2016-2020: the real estate years. Started an Airbnb company with a friend. Sold it in 2020 to move on to the next thing. - 2020-2024: the writing and research years. Worked for a few big startups, wrote biographies billionaires and bootstrappers, explored the world of communities and masterminds. The most lessons and insights. - 2024-2026: the client years. Worked one-on-one with founders as contributor, consultant, and advisor. Mainly equity partnerships and retainers. Seeking PMF, and sometimes finding it. Mainly trying to prevent the same early mistakes I made from sinking ships. Now, I'm building my own things. I've always worked with teams. Turning a new leaf and working on putting out into the world the things I dream. Stay tuned for more.