Early Startup Thoughts from a First Time Founder

The third chapter of my career is my first chapter as an entrepreneur. I’ve been friends with entrepreneurs, coached and mentored entrepreneurs and admired all of them for years. But I don’t think I ever began to understand them until the last few months of my own startup journey. Below, I outline the 4 major lightbulbs I’ve had so far - Courage, Isolation, Struggle and Joy:

💡 COURAGE

If there's one common thread I've seen among founders, it's courage. No matter how much diligence has been done and numbers run, the risk tolerance for entrepreneurs has to be high. In late February, one of my mentors asked me if I had taken any big risks since being laid off. It made me think longer than was comfortable. Maybe being in a company for so long had trained me to draw inside the lines. Granted, that all changed for me on March 1st when I launched my new business, Doyne Services, LLC - Professional Coaching and Career Services. There have been moments of doubt, counterbalanced by self-confidence and the privilege of time, resources and a strategic approach. I have also leaned on the recollection and advice from entrepreneurial friends and my 25 years of sports media leadership experience with innovative projects, product launches, judging startup competitions and hackathons. I know this is in me and truly pales in comparison the courage summoned by others around the world, not just founders but heroes like single parents, our military, front line workers and emergency responders.

💡💡 ISOLATION

This one has hit me harder than I expected. I thought the 2020 Quarantine was good practice for a WFH startup life. That’s true, to a degree. The basement office is fine with me and I get out for periodic coffees and lunches. I also love getting to see my wife, Aimee and our canine therapist, Baxter, throughout the day. I’m a self-declared ambivert and I don’t need tons of people around me or much attention at all. I’m also still getting plenty of fulfilling 1:1 interactions with clients.

So what do I miss? I miss being on a team. I miss the hallway conversations, the spirited debates, group problem solving and generally hanging out with people I respected and enjoyed being around. And I really miss the tremendous functional experts who made our stuff sing. My leadership style has always favored shared ownership. I’m a jack of all trades, master of none type. I found it very natural to lean on my team and internal partners like marketing, creative, tech, legal, product, etc, etc. Now I find myself attempting to be all of those things and it really doesn’t suit me. With some humility, I’m not great in any of those areas but I think I did a pretty good job building and leading teams and businesses.

The solution I’m pursuing now is developing a cast of “phone-a-friends,” advisors and contractors. Legal and Accounting - like the Plumber and Electrician of home improvement - 2 things I would never try myself. Design? Hit me up if you can help. It’s time for a logo, spiffing up my materials and developing the professional panache worthy of the investment being made by my clients. The rest will evolve as the business and scope grows.

💡💡💡STRUGGLE

This part is tough. It’s easy to pretend everything is perfect. I could provide a superficial veneer that is prevalent on social media - only the good stuff. But that’s not life. And it’s definitely not startup life. I can’t claim any major disasters because this all has to be kept in context. I’m in a very good position to start a low capital venture. I also don’t believe suffering is a necessity. Struggle, however, I think there’s some value in it. As likely borrowed from a motivational poster, sometimes you have to go through it to get to it.

Here’s a chart for reference that I picked up during my training with Erickson:

The first step of learning is realizing you don’t know anything - conscious incompetence. Until then, ignorance is bliss. Someday, I’ll be riding this bike with no hands, but I’m not even close yet. I can’t forget that learning comes from failing. I know I will get things wrong and need the fortitude to keep trying new things anyway.

Also a challenge, the emotional swings I was warned about…. The highs are higher and the lows are lower. I haven’t experienced the extremes yet, but this business is very personal for me. My name, my reputation, putting a price on my time. Sink or swim, it’s up to me. 99 days out of 100 I feel great, but there was a day recently that something stressed me out. Thankfully, a peaceful puppy walk at the nature center snapped me out of it and I regained my strategic bearings - falling back on my product development roots and lean startup principles. Launch an MVP. Test and Adapt. Analyze and Iterate. That’s the ticket for me and I know I’ll be fine.

💡💡💡💡 JOY

I can’t lie, it’s nice not having a boss. With all due respect to the great bosses I’ve had, this is just different. What else am I enjoying? The learning. This motivator started to crescendo for me the last few years. Learning by choice is a blast. Neuro-science, human psychology, motivation, clients in different industries, countries, roles. New terminology, learning by doing. It’s like the Couch to 5K. When you’re starting with a low baseline, once you begin, the improvement rate is pretty immediate. Obviously I have a long way to go, but that’s exciting too.

Also, my schedule is more in my control. As I’d hoped, the flexibility has allowed for more time with family. I’m as busy as I want to be and I’m healthier than I’ve been in a long time. Sleeping better, exercising more, meditating longer, eating better. Trust me, I’m no saint, but I’ll take the progress.

As detailed in a previous post, I am immensely grateful for the coaching community who has helped me with my learning and launching. But that’s not all. My family and friends have been there for me. Mini reunions with former colleagues are energizing. Offers of help are ever-present. A kind word, a short text, a note of appreciation, a quick call. Even the little things mean a lot. And as an entrepreneur in a professional services field, the referrals mean so much. It's quite humbling when someone trusts me to help someone they care about.

Lastly, I just plain love the work. Having the opportunity to help several people every day is a privilege and joy.

CONCLUSION:

I’m proud of what I’ve accomplished so far and thankful that this new calling pierced my consciousness at exactly the right time. As for life as an entrepreneur, it’s the journey not the destination. But I have to admit this revenue chart makes me smile. Going from zero to more than zero is quite a feeling. Let’s go!!

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