In this episode we talk about strategic financing options. There are a lot of ways to raise money for your startup, and corporate investors (strategics) can be a good option. Are they right for you? What are the pros and cons of strategic investment? We are here to help! In this episode we answer questions including:

• Should you raise money from a competitor?
• What about raising from your customers?
• Are government grants a good idea?

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Your hosts:

• Sean Byrnes: General Partner, Near Horizon www.nearhorizon.vc
• Ash Rust: Managing Partner, Sterling Road www.sterlingroad.com
• Nic Meliones: CEO, Navi www.heynavi.com

Reminder: this is not legal advice or investment advice.

Q1: Should you raise money from a competitor?

Sounds risky, huh? Your instinct is probably right—this is a red flag! Conduct a principled evaluation. Recognize the opportunity while weighing strategic upside versus structural risk.

Here's the key: your competitors' motivation to invest in you is likely not aligned with your needs. They are not loyal to you, thus there are other incentives guiding their interest in investing. There are potential espionage risks and conflicting incentives that can cause significant issues later, especially if your startup becomes big.

The good news: you can say "no!" Competitor interest is a signal. If competitors want in, perhaps other better-suited investors will too.

Q2: What about raising from your customers?

Customer interest is validating, but tread carefully. Customer investors are risky. Information rights can severely hurt your negotiating position. Furthermore, if your customer-turned-investor churns, that can significantly hurt your market credibility.

Delay such conversations until later in the round. If you decide to raise capital from your customers, structure the investments thoughtfully, possibly through RUVs or uncapped terms. Clearly define boundaries to help manage risks while preserving relationships.

Q3: Are government grants a good idea?

Grants are not fundraising red flags. In fact, securing a grant can often signal market validation. Investors love dilution-free capital. However...while dilution-free capital is attractive, beware of grants that work outside your strategic roadmap. This can become a distraction.

While grants demonstrate external demand, their slow processes can divert focus from iterating on core product-market fit milestones. Grants are strategically advantageous only if they accelerate your core objectives rather than redirect them.

So, ask yourself: "Does the grant move us forward on our roadmap? Or does it give us a new roadmap?"

Your answer to that question gives you all the clarity you need.

In this episode we talk about co-founders. If you start a company, chances are you have a co-founder. How do you maintain a positive relationship? What happens if you start fighting? We are here to help! In this episode we answer questions including:

• What happens when you never agree with your co-founder?
• How do you handle a co-founder who lacks commitment?
• What happens when one co-founder is working harder?

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Your hosts:

• Sean Byrnes: General Partner, Near Horizon www.nearhorizon.vc
• Ash Rust: Managing Partner, Sterling Road www.sterlingroad.com
• Nic Meliones: CEO, Navi www.heynavi.com

Reminder: this is not legal advice or investment advice.

Episode 50! We've answered hundreds of your questions and now it's time for us to tell you more about our journeys. In this episode we dive into our own experiences as founders including:

• What is the worst crisis we faced as founders?
• What was the highlight of our founder experience?
• What's the craziest thing that happened to you as a founder?
• If you could go back in time, what's one piece of advice you would give yourself?

Next episode we'll be back to answering your questions! You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Your hosts:

• Sean Byrnes: General Partner, Near Horizon www.nearhorizon.vc
• Ash Rust: Managing Partner, Sterling Road www.sterlingroad.com
• Nic Meliones: CEO, Navi www.heynavi.com

Reminder: this is not legal advice or investment advice.

Q1: What is the worst crisis we faced as founders?

We kicked things off with true tales of turbulence. Ash faced a startup-ending crisis when a strategic investor pivoted to acquire a competitor. What followed? 50 first meetings with potential acquirers, months of intense hustle, and a personal commitment that went well beyond normal expectations — all to keep the company alive and secure a successful sale.

Nic's story featured the pain of losing a major customer and a key team member at the same time. What followed was a period of flailing — chasing ideas without a clear process. The lesson? Without startup fundamentals like customer discovery, you’re just throwing spaghetti at the wall.

And finally, Sean explored the dreaded moment when a startup is close to insolvency. Do you push forward or shut it down? In this case, the team pushed through — and landed a huge acquisition. But the lesson: there’s no universal answer. The line between "pivot" and "persevere" is razor thin.

Q2: What was the highlight of our founder experience?

We featured:

The emotional closing dinner after a sale, where team members called it the “best job of their life.”

Watching real users find joy in your product — including one user who still keeps the original email from your startup pinned as the only item in her inbox.

Celebrating big wins under pressure, like raising $2M in two weeks after a well-prepared YC Demo Day showing.

These moments remind us that founder glory is real — if rare and hard-earned.

Q3: What's the craziest thing that happened to you as a founder?

How about accidentally hiring a real-life con artist who faked her way into the team? That's the infamous Shirley Hornstein saga.

What about taking a cold call only to be berated by none other than Steve Jobs?

And we discussed moments of serendipity: attending the very first Bitcoin conference, winning its hackathon, landing first customers on the spot, and picking up investors the same day.

The lesson? Overcome mistakes. Build resilience. Be in the room. Make luck happen.

Lightning Round: If you could go back in time and tell yourself one thing before becoming a founder, what would it be?

• Obsess over the problem, not the solution.
• Seek out the smartest people and learn from what they're learning.
• Don’t split your attention. One great product > two mediocre ones.