Angel Club MasterClass: Fundraising & Pitching with Angel Club Mentor Mike Sherbakov

TL;DR: 

Mike Sherbakov’s journey from Marine to venture capitalist is packed with tactical wisdom for founders. His masterclass reveals that investors seek founders who prove traction, demonstrate resilience, and lead with authenticity. Success hinges on building genuine relationships with investors, showing measurable progress, and communicating with clarity and consistency. Execute relentlessly, treat fundraising as a marathon—not a transaction—and remember: the qualities that set you apart aren’t just desired—they’re required.

From Marine to VC: Mike Sherbakov’s Lessons for Founders

The path from military service to venture capital isn't exactly conventional, but Mike Sherbakov's journey proves that unconventional can be extraordinarily valuable. As someone who's managed to build a $20M portfolio and established The Veteran Fund, Mike brings a unique perspective to the startup world—one that's equal parts battlefield-tested wisdom and Silicon Valley savvy.

His recent masterclass delivered actionable intelligence for founders navigating today's brutal fundraising landscape. Here's what every founder needs to know from someone who's seen both sides of the investment table.

The Evolution of an Unlikely VC

Mike's transformation from U.S. Marine to venture capitalist wasn't a straight line—it was a masterclass in resilience and adaptation. After completing his military service, he dove into the entrepreneurial deep end, spending a decade building companies in health and wellness.

The journey included both spectacular successes and brutal failures. His brick-and-mortar franchises and e-commerce ventures provided valuable wins, but it was his venture-backed startup, Wildfire, that delivered the most expensive education. The company's failure wasn't just a setback—it was an MBA in what actually separates successful startups from the casualties.

Today, Mike operates with laser focus through the Veteran Fund, investing specifically in military veterans building critical technology companies at the seed stage. His investment philosophy is simple: find exceptional founders solving real problems, then bet big on their ability to execute.

The Brutal Reality of Today's Fundraising Environment

Let's address the elephant in the room: fundraising has become exponentially harder. Mike's firm alone reviewed 5,000 companies to make just 25 investments from their first fund. Those odds aren't just challenging—they're absolutely brutal if you're unprepared.

The landscape has fundamentally shifted. What used to work five years ago—a compelling vision and charismatic founder—isn't nearly enough today. Investors are drowning in deal flow, and they've raised their standards accordingly.

The Three Pillars Every Investor Evaluates

Mike breaks down investor evaluation into three critical areas: team, product, and market. But here's where most founders miss the mark—they think these three elements carry equal weight. They don't.

"If you have a chart in your deck going up and to the right, most investors will take that meeting," Mike reveals.

Traction has become the ultimate trump card. Revenue growth, customer acquisition metrics, pilot program results—anything that demonstrates real demand signal immediately elevates you above the competition.

But what happens if you're still in the pre-traction phase? Mike doesn't leave early-stage founders hanging. You need to convince investors that you're the outlier founder—the one who defies the odds through unique industry insights, exceptional background experience, or deep understanding of a problem others completely miss.

Fundraising Isn't Transactional—It's Relational

Here's where most founders catastrophically misunderstand the process. They approach fundraising like they're applying for a business loan when they should be courting a life partner. The moment you accept outside capital, you're signing up for a decade-long relationship with someone who will influence your major decisions.

"It really is a relationship," Mike emphasizes with conviction.

"Just like a marriage, you don't meet someone and on the first date ask them to marry you. You have to get to know them"

This isn't just feel-good advice—it's strategic intelligence. Understanding the relational nature of venture capital transforms how you approach every interaction, from initial outreach to due diligence to closing.

The Magic Words That Signal Success

After your first investor meeting, there are three words you want to hear above all others: "Tell me more."

This simple phrase signals genuine interest and opens the door to deeper conversations. It means you've passed the initial screening and earned the right to a follow-up.

Mike suggests treating each investor interaction as an opportunity to build confidence and rapport. Every conversation should leave the investor thinking:

"This is the founder I want to bet on."

The De-risking Mindset: Understanding How VCs Think

Venture capital is fundamentally about risk management. The earlier the stage, the higher the risk—and potentially, the higher the returns. Understanding this dynamic gives founders a massive psychological advantage.

"Every data point, when I'm having a conversation with a founder, I'm hopefully de-risking that investment in my mind," Mike explains.

This means every single interaction matters. Do you follow through on commitments? Are your financial projections realistic? Do you demonstrate integrity in small details?

These evaluations extend beyond formal meetings. Mike admits to checking founders' social media profiles during due diligence, looking for consistency and focus. If your online presence suggests you're juggling multiple ventures or lack commitment, that's an immediate red flag.

The Qualities That Actually Close Deals

What separates fundable founders from everyone else? Mike's answer draws from his military background but applies universally: leadership, resilience, and unwavering purpose.

"We look for someone with incredible drive and vision," he explains.

The Veteran Fund specifically targets military veterans because they've already demonstrated these qualities under extreme pressure. But non-veteran founders can showcase similar characteristics through their track record of overcoming challenges and consistently delivering results.

Tactical Mastery: Communication Strategies That Work

Mike shares battle-tested communication tactics that can immediately improve your investor interactions. These aren't theoretical concepts—they're proven strategies from someone who's successfully navigated both sides of the investment equation.

The Multi-Platform Outreach Revolution

Most founders make a critical tactical error: they rely exclusively on LinkedIn for investor outreach. Mike reveals the insider approach:

"Every single investor that you speak with, if you think they're a good fit for you, find them across all social media platforms."

Different investors prefer different communication channels. Mike personally maintains inbox zero on email but uses auto-responders on LinkedIn due to overwhelming volume. The lesson? Research your targets and meet them where they're most responsive.

The Perfect Investor Call Framework

Here's a game-changing structure for investor calls. After brief pleasantries, Mike recommends this exact approach:

"I know we have 25 minutes left. I have a deck ready, but how would you like to run this call?"

This simple question puts the investor in control while demonstrating thoughtfulness and respect for their time. Some investors want the full presentation; others might dive straight into specific slides covering traction or team composition. Flexibility shows professionalism and strategic thinking.

The Follow-Up Game: Your Secret Competitive Advantage

The real magic often happens after the initial meeting concludes. Mike shares a powerful strategy that's led to multiple investments in his portfolio: the systematic investor update approach.

"End every investor call by asking, 'I would love to keep you updated on our progress, are you okay if I add you to my investor updates?'" Mike reports a 99% acceptance rate to this question.

Crafting Updates That Convert

What makes an investor update effective? Mike's formula is deceptively straightforward: keep it short, sweet, and bottom-line focused. Investors are busy people who appreciate concise communication that highlights key metrics, major milestones, and specific needs.

The update serves dual purposes: it keeps you top-of-mind when the investor is ready to make decisions, and it demonstrates consistent execution over time. Many of Mike's investments have come from founders who stayed in touch through regular updates, proving their ability to execute on their vision.

The Veteran Advantage: Lessons for All Founders

While Mike's fund specifically targets veteran entrepreneurs, the qualities that make military founders attractive apply to all successful entrepreneurs. Veterans bring a unique combination of leadership experience, resilience under pressure, and mission-focused execution.

"Military veterans have already demonstrated their ability to perform under extreme stress and lead teams toward common objectives," Mike notes.

These same qualities—leadership, resilience, and unwavering commitment to mission—are exactly what investors seek in any founder, regardless of background.

Live Session Highlights: Feedback from Our Audience

Here is some feedback shared by participants after our live masterclass session:

• 5/5 - “Superb hosts. Superb guests. Always in the Angel Club. Thanks to Mike Sherbakov for being such a generous guest, facing founders with tangible tips as we're FAFO'ing our way through all the noise. And a thousand thanks to Team Angel for always having our backs and holding this space.” - Angelique Z.

  
  

• 5/5 - “A truly useful session. Just wish we could have kept Mike in the session for another 3 hours!” -  Nick G.

  
  

• 5/5 - “Great event. Thank you for organizing!” - Salma S.

  
  

Take Your Next Step with Angel Club

Ready to leverage these insights and fuel your entrepreneurial journey?

Join us for an upcoming mentor masterclass at angelclub.com/events, or pitch the syndicate at angelclub.com/syndicate.

Explore other investors and resources that might be a perfect fit for your goals using our public resources. Want more? Gain access to exclusive lists and resources available only inside Angel Club.

Curious about what membership can offer you? Learn more about the benefits of joining Angel Club.

Looking for mentorship? Check out our mentorship page to discover a curated selection of our mentors you can connect with as a member.

When you’re ready to scale your vision with support and resources tailored for ambitious founders, we’re here to welcome you into the club.