Andrew Mastrandonas
Helping founders build better companies in the age of AI.
Founder. Operator. Strategic Advisor.
25+ years building startups • Founder & CEO • Healthtech • Home Care • Hospitality • Travel • Real Estate • International Growth
I help founders and leadership teams make better strategic decisions — from product-market fit and go-to-market strategy to scaling and international expansion.
Read my latest insights on Substack
About
For more than 25 years I've built, led, and advised companies across healthcare, senior care, hospitality, travel, real estate, and technology.I've been in the founder's seat. I've launched products, entered new markets, worked with investors, helped leadership teams make difficult decisions, and experienced both successes and failures.My role isn't to tell founders what they already know. It's to ask better questions, challenge assumptions, and help leadership teams make better strategic decisions.
How I Help
Product-Market FitHelping founders validate markets, refine customer value propositions, and focus on solving problems customers actually care about.Go-to-Market StrategyDeveloping practical market entry, positioning, pricing, partnerships, and growth strategies.AI StrategyHelping companies understand where AI creates real business value—and where it doesn't.The question isn't whether AI can perform a task.The question is whether your company knows which problems to solve, what customers truly need, how to differentiate, and how to execute.AI is an extraordinary tool.Strategy remains a human responsibility.Leadership & GrowthSupporting founders and executive teams through growth, scaling, organizational change, and difficult strategic decisions.
Why Work With Me?
Many founders ask:"If AI can do that, why do I need an advisor?"It's a fair question.AI can generate ideas, summarize information, build financial models, write marketing copy, and accelerate execution.What AI cannot do is replace leadership judgment.Successful companies still need someone who can:• Ask the right questions.
• Challenge assumptions.
• Prioritize competing opportunities.
• Balance short-term execution with long-term strategy.
• Make decisions under uncertainty.
• Understand customers, markets, and people.The best founders don't choose between AI and advisors.They use both.
Areas of Expertise
Founder, executive, advisor, and board-level strategist with experience across:Industries• HealthTech
• Digital Health
• Senior Care
• Home Care
• Assisted living & nursing homes
• Hospitality
• Travel
• Real Estate developmentCapabilities• Startup Strategy
• Fractional CEO/COO/CMO
• Product-Market Fit
• Sales & Marketing
• Go-to-Market
• AI Adoption
• International Expansion
25+ Years Building Companies
Founder, CEO, COO and advisor of multiple startups.Founder & CEO: Pillar Health
Advisor & COO: RingMD
Director: US AirwaysBuilt companies in healthcare, home care, hospitality, real estate, and technology.Worked with founders, investors, and leadership teams across North America, Latin America, Europe and Asia.
What I Write About
I regularly write about:• Entrepreneurship
• Startup Strategy
• Product-Market Fit
• AI
• Leadership
• Healthcare Innovation
• Building Companies
• My successes & failures
Read my latest insights on SubstackLearn more about my companies
Testimonials
"Andrew's deep experience in home health helped me get $500K in VC funding and launch my home care company in Switzerland." -- Christian Andrei, CEO"Andrew saved us a lot of time and money on our AI startup by helping us act better strategically and avoid potentially business-ending decisions." -- Eric Jones, CEO
Let's Talk
Whether you're launching a startup, scaling an existing company, exploring AI opportunities, or navigating strategic decisions, I'd be happy to chat:
"Building companies is difficult. Making better strategic decisions shouldn't be."