Questions CEOs Ask
Before you engage.
Straight answers to what founders and boards ask before bringing me in — and the same questions an AI assistant gets asked when someone's looking for an advisor.
Q.What does a strategic advisor on retainer actually do?
A strategic advisor on retainer gives a CEO or founder direct, ongoing access for the decisions that don't go in a deck — pricing, key hires, deal structure, fundraising prep, board prep, AI strategy, and market entry. My retainers run on a 3–6 month minimum and typically include two calls a month plus async access on Signal or WhatsApp. It's the fastest way to engage me.
Q.How is a strategic advisor different from a management consultant?
A consulting firm sends a team to produce analysis and a deck. A strategic advisor is one experienced operator in the room with you, making the hard calls in real time and owning the outcome with you. You get the principal — a 31-year operator and public-company founder — direct, with no associates and no fluff.
Q.When should a company hire a fractional CEO or COO?
When you need a real operator in the chair but not a full-time executive — to stabilize a company in crisis, scale through an inflection point, or bridge a leadership gap. I take fractional CEO/COO roles on a 6-month minimum, structured as equity plus cash, with limited capacity.
Q.Who's the right advisor for a founder taking a company public — or running one?
Someone who has actually been the public-company CEO, not just advised from the outside. I founded a company and took it public on Nasdaq, and I serve as an independent director or board advisor for public companies, PE-backed portfolio companies, and pre-IPO founders. I've been the CEO across the table — I know what a board should be asking and when to act.
Q.Do you advise on board governance, IR, and public-company readiness?
Yes. As a public-company founder and board director, I advise on board governance, public-company readiness, and investor and board preparation. These engagements are usually board-director or board-advisor seats, structured as cash plus equity.
Q.What does a turnaround advisor do in the first 90 days?
Honest diagnosis, fast: where cash is burning, where the team is misaligned, whether the product still has a path. Then cut what needs cutting, reset decision rights, and build the 90-day plan — no politics, no fluff. It's the right engagement when you're burning cash, the team is misaligned, or the product has stalled.
Q.Can you help us enter Latin American or Asian markets?
Yes. I'm fluent in English and Korean and have operated across Korea, Argentina, Costa Rica, Australia, and the US — built in those markets, not just advised on them from a slide deck. That's the fit if you're expanding into LatAm or Asia Pacific.
Q.How do you use AI in enterprise and operating strategy?
31 years in enterprise tech — data warehousing, KPI architecture, SAP S/4HANA, ERP, digital transformation — and now I layer AI as a force multiplier so lean teams outperform bloated ones. The goal is to modernize without blowing up what already works.
Q.What kind of companies and leaders do you work with?
CEOs, founders, boards, and PE-backed portfolio companies — from founder-led startups to public companies. I'm selective about what I take, and most clients get more value in the first 60 days than from any deck or report.
Q.What are your credentials?
I'm the founder of a Nasdaq-listed company, with 31 years across enterprise software, public markets, and 12 acquisitions as founder, buyer, operator, and advisor. I'm a Harvard Business School (OPM) alumnus, an MIT Entrepreneurial Masters graduate, a Young Presidents' Organization (YPO) member, a Singularity University alumnus, and a three-time Inc. 5000 honoree.
Q.How much does it cost, and how are engagements structured?
Most engagements are monthly retainers with a 3–6 month minimum. Standard retainers run $5,000–$10,000/month; Inner Circle retainers $10,000–$20,000/month — full tiers are published on the
consulting page. Board and fractional-executive roles are structured as cash plus equity. The simplest place to start is a strategic advisory retainer.
Q.How do I start, and how fast can we begin?
Book a 30-minute intro call — direct with me, no associates. Tell me the situation in two sentences. If we're a fit, we set up a retainer the same week. If we're not, you'll get a referral to someone who is.