Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Thomas Rosenberg, Founder of ReGenerate Coaching, located in Oakland, CA, USA.

What's your business, and who are your customers?

I work with individuals and teams, addressing friction and communication issues, and guiding them to understand how individual stories shape team/organizational culture, levels of trust, innovation, and growth.

Tell us about yourself

I have always been passionate about helping folks grow and transform. However, coming from a medical and scientific family, I felt the need to pursue a technically challenging career path in order to be seen as a man. As a result, I worked in a variety of sectors and roles, often as a technical subject matter expert, with people and teams from different cultures in over 20 countries on 5 continents. The underlying theme through it all has been helping people, and their organizations become comfortable with change, lead change, and flourish. Although I didn't always recognize it at the time, I instinctually found opportunities to insert myself into coaching situations.

I now realize I took on the subject matter expert role because I didn't feel I could show up authentically. This perception shaped many career and life decisions. Fast forward to June 2014, when I suffered a traumatic brain injury in a near-fatal bicycle accident. It took me over two years to trust my brain again. About that same time, a dear friend passed from cancer. She inspired me because she lived richly, shared all her gifts fully, and died with tremendous grace. I knew I didn't want to continue backing myself into someone else's box. Whatever remaining life energy I had, I wanted to focus on what mattered most to me. I moved towards coaching full-time, which included pursuing my first coaching certification and launching ReGenerate Coaching in 2017.

The ethos of my work is: reconnect to ourselves, so we can more easily connect with each other so that we can reconnect to the planet.

What's your biggest accomplishment as a business owner?

Consistently satisfied clients.

What's one of the hardest things that come with being a business owner?

Being honest with yourself about what you're not as good at and what you'd rather spend time doing. It's easy to be hard on yourself for not being able to do it "all." Noticing where you want to spend more time and what comes naturally actually facilitates your working on your business and asking for help in the areas where you're not as strong.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. In my experience, it's a marathon, not a sprint. I've found entrepreneurship to be a journey of constant growth and consistently stepping outside your comfort zone. Remember to work on the business, not just in the business.
  2. Don't be afraid to ask for help. You'll likely excel at one or even several aspects of your business. It's very rare that someone is equally good at everything a business needs to grow. Ask for help in the areas you're not as good at or comfortable with.
  3. Find community. I have found it invaluable to have a group of friends and former colleagues who are also entrepreneurs. We get together regularly to talk about where we are, what we're struggling with, and recent successes. In addition to just listening, we provide feedback to each other, suggestions for tools, or people who might be able to help with a particular issue. None of our significant others are entrepreneurs, so our regular gatherings give each of us an outlet, a place of shared understanding.

Is there anything else you'd like to share?

As a founder, it's less about time management than energy management. How are you spending your energy? How is it balanced between short-term needs and long-term goals? How are you mapping your multi-year, annual, monthly, and weekly goals?

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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