Services
$200 / month
Start free, decide later
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1
Free 7-day trial
No charge until day 7. Cancel anytime. -
2
Ongoing calls + chat
2 × 30-min calls per month, unlimited Q&A. Replies in 2 days. -
3
No lock-in
Month to month, no contract.
No spots left, but you can save the mentor to your wishlist to get notified about their open spots!
About
I help startup and small business entrepreneurs go from idea to reality, including thinking through your 5 Ts: Technology, Team, Traction, Timing, and Trust.
Most of my coaching has been with Bootstrap / Pre-Seed / Seed founders working a venture-worthy solution, but I’ve also worked with tech and non-tech entrepreneurs building self-funded, quick-to-revenue business. I’ve been a Techstars mentor for years, and I’ve formally and informally mentored dozens of founders for over a decade.
I’ve started four companies and dissolved three. I’ve raised a few million and ridden the VC rollercoaster. I’ve had to fire a co-founder, put a company into bankruptcy, and deal with antagonizing investors. My coaching is a no-judgement zone where it’s okay for you to feel clueless, not be an expert, feel down about challenges, and also celebrate your wins - because those will come too. We’ll focus on your strengths, resilience, and cultivating your learner’s mindset.
I’m also a parent and life partner. Being an entrepreneur is impossible to separate from our other primary roles, and I provide a safe space for you to talk freely about how to balance it all.
My style of mentoring is to listen carefully, empower you to vent in a safe space, help you see patterns and potential pitfalls, and shine a light on your strengths and assets you might not see in your moments of “not knowing.” You bring your curiosity and vulnerability, and together we’ll talk through whatever is blocking you, so that you can figure out a strategy for next steps.
Mentoring requires a “click” between the mentee and the mentor. I encourage my mentees to schedule a bit of time with a few different mentors to find that click. The first step is always to be brave and curious, and to reach out for some fresh perspective.
What mentees say
5 out of 5 stars
Maciej
Standard Plan • 4 months
What happens when you start
You tell Diane your goals. They see exactly what you want to work on before session one.
You meet within days. Diane reviews your application and books your first session, usually within a day or two.
You leave with a plan. Concrete next steps and a weekly rhythm from your very first week.
