Turning a "Talks Too Much" Kid into a Founder Who Closes

What if the trait you were taught to hide is the one your business needs?

The conversation she wasn't supposed to be having

"I was supposed to be working on the flight. Instead I spent the whole time talking to the person next to me, and now I have a sales call with them next week."

She told me this like she was confessing to a failure, one that went all the way back to her report cards that always read, "Talks too much in class.” The sales call barely registered because of the shame she had internalized around her ADHD.

She had a real gift for ideas (she could sketch a fundable business over coffee and make you want to invest on the spot) and an equally strong tendency to talk herself out of them. A voice in her head kept telling her that a brown woman with caregiving responsibilities needed to work for someone else, earn the PhD, win the contract with a large, stable, well-known organization, and then let those names vouch for her.

The respectable path collapsed beneath her

For a long time the respectable plan felt like the only serious option. Then one of the household-name organizations she had thought was her dream client landed in the headlines for the kind of culture and ethics collapse that instantly erases wealth and reputations. Watching that unfold shook her belief that institutions could ever be her safety net.

Even after she created a business idea that was genuinely fundable and started building toward it, the doubt stayed. She still beat herself up for her burst-and-crash rhythm, even though she understood, at least intellectually, that she was never built for grind culture.

Working through the lows

Being a founder is a roller coaster, and much of our work was about navigating the lows. We worked on the all-or-nothing thinking that turned temporary (although significant) setbacks into proof she wasn’t capable as a founder. We worked on challenging the linear, heads-down model of productivity she kept measuring herself against when a burst and rest rhythm was far more effective and sustainable for her. When the doubt rose, we narrowed the focus to the next concrete step rather than the whole mountain.

Over the months she got better at catching the story in real time. A setback stopped being a verdict on her abilities and became a challenge she could look at with some curiosity. She learned to trace her stuck moments to causes she could name and address, which made the doubt easier to move through and the next decision easier to reach.

Holding her ground as a founder

Our work honored the full reality of who she was rather than treating her caregiving as a problem to be solved around. She was not going to set that part of her life aside to build her business on someone else's terms, and she needed a coach who understood that rather than treating it as a problem to be solved.

The rest was about her boundaries. She got sharper at asking for what she needed and at noticing when a client or partner was treating her as the help instead of recognizing the founder in front of them. She learned to spot the people who genuinely backed her vision versus those who would keep pressuring her to make it smaller, and she chose her partners from the first group.

Where she is now

She is in her first round of funding and on schedule to hit her target. The gift for ideas is still there, and so is the relational instinct that used to feel like a distraction. These days, when she lands a lead from a conversation she never planned, she books the follow-up without apologizing for how it happened.

Testimonials

  • “When I started my role as an Executive Director, I needed guidance and support from someone who would understand my challenges and concerns. My work with Kai has been invaluable and necessary to my growth and evolution as a leader. ”

    — Dorothy R. Santos, Executive Director, Processing Foundation

  • “When I left my corporate job, I didn't anticipate how much I relied on the structure someone else had built for me. Suddenly there was no project manager or regular schedule. I had plenty of ideas, but no idea on how to move them forward. Working with Kai helped me figure out how to build that structure myself, on my own terms.”

    — Maryann Bell, Maryann Bell Coaching

  • “Kai’s leadership coaching has made a lasting impact on both my career and my life. His approach is grounded in a deep commitment to understanding who you are, what motivates you, and the values that guide your decisions.”

    — Kevin Kovalski, AVP, Communications at ASU

  • “Kai is both empathetic to each person’s perspective, as well as thoughtful in his analysis and research. This combination really provides outstanding diagnostic as well as heart-driven solutions.”

    — Seema Chauhan, Human Resources Business Partner, Infineon Technologies

  • "I'm beyond grateful for Kai's keen insights during our coaching sessions. Kai brings a grounded presence to his coaching work. He creates a safe, supportive space for vulnerable, meaningful conversations and asks perceptive, open-ended questions that encourage self-reflection and growth within one's unique leadership journey."

    Susan Hagness, Dean Designate, Case Western Reserve University

Who I’ve worked with