In this episode we talk about venture capital (VC) firms. Many startups want to raise funding from VCs, but how do VC fund make decisions? How do they think about companies? What goes on behind the scenes after you pitch at VC? We are here to help! In this episode we answer questions including:

• What steps do VC firms follow to make an investment?
• What happens when VC partners disagree on an investment?
• What exactly are VC firms looking for?
• What are VCs measured by?

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: What steps do VC firms follow to make an investment?

The top of the funnel is massive. It includes founders reaching out cold via email, warm intros from fellow founders, and meetings at conferences. The "email filter" is usually the first point of contact.

From there, the process typically looks like this:

• First Meeting
• Meet the Team
• Team Decision
• Diligence

The funnel narrows at every stage, filtering out 99% of companies. The "golden ticket" is a warm intro from a proven founder. That being said, if you lack a network, you must not shy away from cold outreach – but your pitch must be exceptional to survive the filter.

Q2: What happens when VC partners disagree on an investment?

Understanding the decision process is key. Do they need consensus, or can a single partner push a deal through? During your first meetings, do your own diligence to ask how the firm makes decisions.

You need at least one partner who is obsessed with what you are doing. Treat your lead partner as your internal co-conspirator. Once you leave the room, they have to go to bat for you against skeptics. Don't just pitch your product; pitch the arguments they will need to use to convince their partners to say "yes."

Q3: What exactly are VC firms looking for?

VCs work on behalf of Limited Partners (LPs) to produce returns that beat the market. Because of the Power Law, one win must pay for all the losses in the portfolio.

Therefore, VCs want companies that can grow fast for a long time. They are looking for:

• A Massive Market
• Competitive Advantage (Defensibility/Tech)
• High Velocity

In short, they need proof that the startup has the capacity to achieve escape velocity. This includes a stellar team, strong product engagement, and an acceleration of product adoption.

Q4: What are VCs measured by?

Ultimately, it comes down to DPI (Distributed to Paid-In Capital). This is actual cash returned to investors. When a VC has good numbers on this, it’s all they talk about.

Before DPI, LPs look at interim metrics:

• MOIC (Multiple on Invested Capital): Paper gains on the money invested.
• IRR (Internal Rate of Return): A measure of the speed of growth of investments.

However, for a VC to actually get paid, they need DPI. They need to return the fund multiple times over. Liquidity matters.

In this episode we talk about growth. Every startup wants to grow faster, but how do you do it? What channels are better than others? Are there secrets to growth? We are here to help! In this episode we answer questions including:

• Are paid ads a good idea?
• How do we scale inbound traffic?
• What drives customer referrals?

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.

In this episode we talk about team structures. As soon as you have employees, you need to decide how to organize them. What are the best organization structures? What are the trade offs? We are here to help! In this episode we answer questions including:

• How many people should you have reporting to you?
• When should you hire leaders like a VP of Sales?
• Do you need product managers?

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: How many people should you have reporting to you?

As a startup CEO, you have to delegate management to avoid becoming a bottleneck. The absolute maximum number of people that should report to you at the early stage is 10. A good rule of thumb is to consider how many one-on-one meetings you can realistically handle every two weeks.

Your first hires should be leaders who can build and own major functions of the company, such as product, engineering, or sales/marketing. These leaders provide leverage, freeing you up to focus on other critical areas of the business. Managing too many people or managing people who are not leaders of their own functions can prevent you from executing on your core responsibilities. Remember, you want to hire exceptional people to do important work in areas you can't or don't want to do alone.

Q2: When should you hire leaders like a VP of Sales?

Hire a leader before your time becomes a bottleneck, but be careful to hire the right person at the right time. A "VP of Sales" is typically a scaler, not a builder. They will likely burn out or fail if your company's sales playbook isn't already baked.

Founders should own the sales process until it's proven and repeatable. Bring in a VP of Sales when you have a clear Ideal Customer Profile (ICP), have closed multiple deals beyond the initial founder hustle, and can hand them a clear playbook instead of a puzzle to solve.

For a sales team of 5-10 people, a Director of Sales with 3+ years of experience is often sufficient. For a team of 10+, you'll likely want a VP with 5+ years of experience. Find someone who can run the sales team better than you can, allowing you to focus on other aspects of the business.

Q3: Do you need product managers?

There is a lot of debate on this! Don't hire a product manager too early. The CEO is the de facto Product Manager (PM) until you achieve product-market fit (PMF). The learning loop is too critical to delegate at this stage.

You know it's time to hire a PM when:

• Customers love your product and keep using it.
• You're seeing organic growth or referrals.
• Engineers are spending too much time in product discussions instead of building.

A PM's role is to be the voice of the customer and ensure engineering time is used effectively. The need for an early PM can also depend on your product. For example, a consumer product may need a PM earlier than a developer-focused tool.

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.

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.

In this episode we talk about staying positive. Things constantly go wrong at every startup company. How do you stay positive in the face of bad news? How do you keep your team motivated? We are here to help! In this episode we answer questions including:

• What if your big product launch flops?
• What do you do if your competitor announces big news?
• How can you keep your team focused on the big picture?

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: What if your big product launch flops?

Product launches rarely meet sky-high expectations: normalize the disappointment. Then, reframe the launch as a learning milestone. Even if metrics fell short, you’ve gained valuable data on what resonates (or doesn’t) with customers. Highlight those learnings to your team.

Adopt an “Always Be Launching” mindset. Shift from high-stakes drops to ongoing micro-launches that build momentum. Celebrate the team’s efforts: recognize execution, creativity, and resilience.

Finally, share a clear next step to drive focus and restore confidence. Forward motion beats stagnation when morale dips.

Q2: What do you do if your competitor announces big news?

Your team may feel shaken, but this is your cue to lead with clarity—not comparison. Fundraising is not a win; strategy is.

Remind your team: we’re playing our game. If the strategy is working, there is no need to chase others. Be transparent about your game plan. Explain how you’re building durable advantages, like customer love, product strength, or operational excellence.

Reaffirm your long-term edge. If you’re not raising now, frame that as a strength. Perhaps your growth and margins mean you don’t need to. Teams rally behind leaders who bring context, calm, and conviction.

Q3: How can you keep your team focused on the big picture?

Start with transparency. Let your team know what happened, why it matters, and also how it fits into the bigger picture.

Then reframe: one customer is not your whole trajectory. Point to forward-looking metrics like pipeline growth, retention, and new demand.

Most importantly: market to your team. Use repetition to reinforce your mission and momentum. When the team believes in the future, they stay focused despite setbacks.

In this episode we talk about getting started. Founding a company means you are constantly learning to do new things, like hiring and selling. How do you handle these new situations where you have no experience? How do you avoid mistakes? We are here to help! In this episode we answer questions including:

• How is AI changing the nature of work?
• How do you stay ahead of how fast AI is changing today?
• Will my data advantage still be an advantage in the future?
• Can AI really replace employees for me?

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: How is AI changing the nature of work?

AI has transformed daily workflows across every part of the startup journey. From first drafts of sales and marketing copy, to deep research using tools like ChatGPT and Perplexity, it's become the first step for many creative processes. Internal tooling has gotten faster with tools like Replit and Cursor, while product discovery now often starts with AI instead of Amazon. Whether it’s coding, devOps, or customer discovery, AI gives founders leverage.

Q2: How do you stay ahead of how fast AI is changing today?

The key is to stay focused on your customer. While tech shifts rapidly, true customer pain changes slowly. Solve real, urgent problems—and use AI tools along the way to stay nimble. It’s totally fine to use APIs like OpenAI’s or wrap an existing model. The winning strategy? Build something valuable today, and keep evolving it with your users.

Q3: Will my data advantage still be an advantage in the future?

"Proprietary data" is losing its edge. Even Bloomberg's private GPT underperformed public models. Unless your data is restricted, hyper-niche, or massive, it's probably not a moat. What matters more is how well you deliver value to users—accuracy, speed, experience, and reliability. That’s your real advantage.

Q4: Can AI really replace employees for me?

It’s not about replacing people—it’s about hiring the right combination of people and AI. Founders need to build the muscle of managing both. The real opportunity is in learning when to hire a human, and when to "hire" an AI tool. Treat AI as an employee that never sleeps, but still needs thoughtful management. We are already seeing plenty of instances where founders are using AI to replace content marketing teams. Furthermore, there is a trend towards smaller engineering teams, with engineers using AI tools to complement and accelerate their efforts.