venture capital
Venture capital is more than funding. It's a relationship that shapes your company's trajectory, board dynamics, and your psychological experience as a founder. Understanding how VCs think and managing those relationships is critical. Raising venture capital changes everything. Pressure intensifies. Stakes get higher. Your relationship with control shifts. These posts explore navigating fundraising, managing investor relationships, maintaining sanity while building venture-backed companies.
The Founder’s Guide to QSBS: Understanding the 2025 Updates and Avoiding Costly Mistakes
A short review of one of the most misunderstood parts of startup compensation: qualified small-business stock.
How to manage your mind while fundraising
Why it is so hard, and what to do about it.
When there is a 95% chance you make nothing: how preference stacks work in startups
The un-examined psychological challenges of the preference stack (and what to do about it.)
Leadership Vulnerability: The Self-Doubt Every Founder Feels but Nobody Talks About
Leadership vulnerability is more common than startup culture suggests. Almost every founder I coach carries the same fear: someone else could do this better, they are not truly qualified, and the gap between how they appear outside and feel inside feels impossible to close. You are not alone.
The myth of the impervious leader
Those founders you read about in the press and idolize? Yep, they are up at 3 AM too.
Struggling to Raise Venture Capital? The step you may be missing.
Most founders I meet have a missing step in their plan for raising capital. The result is frustration and isolation.
The Away Debacle: Is Judgment the Answer to Leadership Accountability?
Leadership accountability demands more than outrage. Here is what it actually requires.
How to find great advisors for your startup (and avoid the bad)
The advisory relationship is one of the most helpful and misunderstood relationships in the startup world. Here’s my personal take on how to get the best out of an advisory relationship from either side.
Startup CEO Coaching: Why I Coach Startup Leaders
Startup coaching is not therapy or consulting. It is a confidential partnership that helps founders make better decisions under pressure. I coach first-time CEOs, venture-backed founders, and startup leaders facing isolation, conflict, or burnout. The work focuses on decision quality, team alignment, and leadership capacity. If you want the story
How to Be a Better CEO, The Hardest Change Great Leaders Make
Tears rolled down my face. I walked down Sandhill Road next to the famous venture capitalist who only days earlier had handed me a generous term sheet. Now, I was telling her my life was falling apart and explaining why she’d likely want to pull the term sheet and work with someone else.
