Interested in starting your own entrepreneurial journey in coaching but unsure what to expect? Then read up on our interview with Trystan Reese, Founder of Collaborate Consulting, LLC, located in Portland, OR, USA.

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

Issues of diversity, equity, and inclusion are complicated. There is both an art and a science to creating inclusive workplaces, and Collaborate Consulting is designed to teach and lead organizations through the most effective processes to improve equity across the board. We facilitate powerful conversations, lead transformational workshops, and coach managers to show up as their best selves with their teams. Using the practices of adult learning styles, somatic awareness, and the science of behavior change, Collaborate Consulting manages to bring energy and joy to the serious work of inclusion in the workplace!

Tell us about yourself

I cut my teeth in the LGBTQ political movement, traveling the country and leading teams of volunteers to beat back our nation's most brutal attacks on the LGBTQ community. Along the way, I became a trained anti-racism facilitator and learned how to change hearts and minds on complicated issues like LGBTQ inclusion. After many years in the nonprofit sector, I left to start my own business. I believe in the power of storytelling, the importance of connection, and a fully evidence-based approach to the work of diversity, equity, and inclusion.

What's your biggest accomplishment as a business owner?

When I started my business, I made it my mission to "go where the love is." After many years of working with people who were resistant to the idea of change, I decided I only wanted to work with organizations that were ready to embrace change. No one magically knows how to transform a work environment, but that's okay because I do! I only require that there is a will to learn and grow and be humble -  and I'm proud to say that every client I've ever had embodies that ethos. I've been able to go where the love is and do my most profound work in the places where I'm most needed.

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

I think of myself more as a creator than a business owner, so it's been harder for me to wrap my head around this role's more "business-y" aspects. I started paying everyone on my team as much as possible and hiring contractors to help with everything. I truly wanted to spread the wealth around and lift up others in the process. But without a true business model, I eventually realized that I had actually to have a budget and a plan - otherwise, there would be no firm at which to employ people! So I scaled back, did more work on my own, and hired only when I needed to and could afford it. This way, I'm more sustainable over the long term and will be able to offer jobs to others (and support my family!) for years to come.

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

  1. Figure out what you're really good at, and build a business from there. Potential clients will come to you asking if you can do this or that, usually because you have a great reputation or they know you and like working with you. But what seems like "easy money" isn't easy if you have to build out a whole new offering from scratch or if you'll have to hire a lot of subcontractors to help you. Better to identify what is your special magic and focus your efforts there, so you'll always be confident you're delivering the absolute best to your clients.
  2. Get business help! There are so many details to manage - getting insurance, paying taxes, licensing fees, employment expenses (taxes, unemployment insurance, disability, etc.), and much more. Find an operations person who can help make sure you're on track.
  3. Don't spend all your money in one place. It can be tempting to get the absolute best of something, be it cloud storage or project management software. But when you're starting out, get the bare-bones version to try out. I've wasted thousands of dollars paying for a year of some software that didn't end up being what I needed -  make sure you LOVE a tool before investing in it.

Is there anything else you'd like to share?

As a transgender business owner, I believe supporting companies owned by marginalized community members is important. It's harder for us to get loans and grants, find mentors and guides, and secure big contracts when competing against larger firms. I hope people keep that in mind when shopping for businesses to work with and support!

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.

Turn your craft into recurring revenue with Subkit. Start your subscription offering in minutes and supercharge it with growth levers. Get early access here.