Winning in the Age of AI: An Investor's Playbook for Building Trust
Key insights from investor and author Razy Shah on why human connection is your new competitive advantage.
We recently had the pleasure of hosting Razy Shah, Venture Partner, Angel Investor, and Author of Winning in the Age of AI, for an insightful session with our BonBillo community. In a world where AI can generate a polished pitch deck in minutes and write code on command, Razy posed a critical question: What truly sets a startup apart? His core message resonated deeply with our philosophy at BonBillo. As AI commoditizes skills, the real edge for any founder is no longer just the technology, but the trust they build, the relationships they nurture, and the conviction they demonstrate through execution.
As Razy puts it, If AI can make it, it can't set you apart.
It means the soft skills - communication, consistency, and coachability - have become the new hard currency. Here are the actionable takeaways from our session on how to build the trust, reputation, relationships and human connection that give you a competitive edge.
The New Rules of Visibility: Show Your Work and Feed the Machines
In the past, many founders believed that if they built a great product, the world would beat a path to their door. Razy argues this is no longer enough. In a noisy market, you have to build in public, not for vanity, but for visibility.
He shared his personal playbook of posting on LinkedIn three times a week, guided by a powerful mantra: I don’t post to be seen. I post so the right opportunity can find me.
This isn’t about chasing clout; it’s about creating a consistent signal that allows potential investors, partners, and talent to discover you. This process compounds over time:
Ideas → Content → Trust → Opportunity
What’s fascinating is that your audience now includes more than just humans. With the rise of AI-powered search and answer engines like Perplexity and Google's AI Overviews, your content is being indexed, understood, and cited by machines. Consistently publishing clear, useful content on platforms like LinkedIn - a top-cited domain by AI - is a form of Answer Engine Optimization (AEO). You are actively influencing what the world’s AI models know about you and your startup, turning your expertise into a new, powerful distribution channel.
Beyond the Screen: The Power of Patience and Proximity
While building a digital presence is crucial, Razy emphasized that the most transformative opportunities often come from long-term, real-world connections.
Two principles stood out: playing the long game and being in the right rooms.
Play the Long Game
In a world of instant gratification, it’s easy to chase quick wins. But Razy reminds us that the most significant deals are like orchards: they are planted years before they are harvested. He shared a story of teaching a steamboat restaurant owner about Facebook marketing for a small fee in 2017. Four years later, that same person, now in a new role, brought him a six-figure opportunity. The lesson is clear: every interaction, no matter how small, is a seed. Nurture your relationships consistently, even when there’s no immediate payoff. An investor's "no" today could become a "yes" tomorrow if you cultivate the relationship with patience and value.
Be in the Right Rooms
Proximity is power. While LinkedIn and email are essential tools, they cannot replace the serendipity and depth of in-person connection. Razy shared how his partnership with BonBillo began not with a cold email, but by showing up at a startup demo day to support another founder. That single decision to be physically present in the right room led to a conversation, a discovery of shared theses, and ultimately, a lasting collaboration. Founders should step away from their screens and intentionally place themselves in environments where their potential customers, investors, and partners gather. Contribute before you extract, build genuine connections, and let the power of proximity work for you.
The Investor's Mindset: Substance, Not Polish
With AI tools, anyone can create a beautiful presentation. This has leveled the playing field, making polish a commodity. As Razy emphasized, investors don't confuse polish with credibility. They are looking for substance. To help founders understand what investors really look for, Razy shared his "Founder Scorecard" - a 7-point checklist he uses to evaluate early-stage startups.
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The Founder Scorecard: An Investor's Checklist |
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1. Demonstrable Strong Why |
Are you solving a problem you've personally lived? Investors back founders with a deep, authentic connection to the problem. As Razy says, "Lived it. Felt it. Now solving it." We see this with our alumni like Arifin from MedEasy, whose personal struggles with healthcare access in Bangladesh fueled his mission. |
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2. One-Sentence Clarity |
Can you explain what you do without jargon? If you can't explain it simply, you don't understand it well enough. |
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3. Earned Insight |
What do you know about your market that most people don't? This is your "earned secret," gained from being in the trenches, not from a market research report. |
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4. Pull, Not Push |
Is there real, organic demand for your solution, however small? Are customers pulling your product from you, or are you constantly pushing it on them? |
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5. Resourcefulness Over Polish |
Investors are more impressed by what you've managed to build with limited resources than by a slick deck with no traction. |
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6. Conviction + Coachability |
Do you have a strong vision but remain open to feedback? The best founders balance unwavering conviction with a willingness to learn and adapt. Saying "I don't know" is a sign of strength. |
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7. The 7-Year Test |
This is the ultimate gut check for an investor: "Would I want to receive your monthly update for the next 7 years?" It speaks to the long-term relationship and the founder's endurance. |
Razy's Filters: Common Red Flags
Beyond the scorecard, Razy shared a list of common red flags that are often an immediate "no" for investors.
These are practical pitfalls that founders should self-audit before starting their fundraising journey.
Absentee Building: Building for a market you don't live in (e.g., building a solution for Bangladesh from an office in Sweden). Proximity to the problem and customer is crucial.
Divided Founder: Running too many businesses or projects at once. Early-stage startups require obsessive focus.
Stage Over Substance: Spending more time on the talk circuit and chasing clout than on building and shipping the product.
Going Dark: Being unresponsive on email or WhatsApp for weeks. Communication is a proxy for professionalism and execution.
The Operating System for Trust: Arm Your Champions
How do you build a pipeline of warm investors so you're not starting from zero when it's time to raise? The answer is to arm your champions through a consistent, transparent monthly investor update.
Razy advises adding potential investors to a mailing list 12 to 24 months before you plan to raise and sending them a concise, honest update by the 5th of every month - good or bad.
This simple discipline is your operating system for trust. You are giving your supporters, both current and potential investors, the information they need to advocate for you. When you share a clear, compelling update, it becomes an asset that an investor can use to amplify your success and help attract opportunities.
This process demonstrates transparency, builds conviction, and keeps you top-of-mind. Over time, it can even create a sense of FOMO as investors watch your progress from the sidelines.
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The 7-Point Monthly Investor Update |
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1. TL;DR |
A one-sentence summary of the month. |
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2. Key Metrics |
The same 3-5 metrics every month, with last month's numbers for comparison. |
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3. Wins |
What went well? Highlight progress and milestones. |
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4. What's Hard |
Be honest about your challenges. This builds credibility and gives investors a chance to help. |
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5. Asks |
Make specific, small, and forwardable requests (e.g., "Introduction to 1 CFO at a $50-200M SaaS company"). A warm intro is always better than a cold outreach. |
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6. Cash & Runway |
Be transparent about your financial health. |
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7. Next Month's Focus |
Show that you are forward-looking and strategic. |
Finally, when someone helps you with an ask, close every loop.
A simple follow-up - "Hey, thanks for that intro. We had a great conversation." - motivates your champions to help you again and again. It shows you're organized, respectful of their time, and effective at turning introductions into outcomes.
Your Relationships Are Your Ultimate Moat
The session concluded with a powerful reminder: AI can replicate your skills. It can't inherit your relationships.
In the age of AI, your ability to build and compound trust is your most durable competitive advantage. The frameworks Razy shared aren't just about fundraising; they are about building an enduring company on a foundation of authenticity, execution, and human connection.
If you're a founder building for impact and looking for a community that champions this approach, we invite you to explore our programs: