Should You Raise Strategic Financing?

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.vcAsh Rust: Managing Partner, Sterling Road www.sterlingroad.comNic Meliones: CEO, Navi www.heynavi.comReminder: 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.vcAsh Rust: Managing Partner, Sterling Road www.sterlingroad.comNic Meliones: CEO, Navi www.heynavi.comReminder: 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.vcAsh Rust: Managing Partner, Sterling Road www.sterlingroad.comNic Meliones: CEO, Navi www.heynavi.comReminder: 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.vcAsh Rust: Managing Partner, Sterling Road www.sterlingroad.comNic Meliones: CEO, Navi www.heynavi.comReminder: 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.vcAsh Rust: Managing Partner, Sterling Road www.sterlingroad.comNic Meliones: CEO, Navi www.heynavi.comReminder: 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.vcAsh Rust: Managing Partner, Sterling Road www.sterlingroad.comNic Meliones: CEO, Navi www.heynavi.comReminder: 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.vcAsh Rust: Managing Partner, Sterling Road www.sterlingroad.comNic Meliones: CEO, Navi www.heynavi.comReminder: 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.

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 do I find a co-founder?How do I sell my first customers before my product is ready?How do I hire my first salesperson?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.vcAsh Rust: Managing Partner, Sterling Road www.sterlingroad.comNic Meliones: CEO, Navi www.heynavi.comReminder: this is not legal advice or investment advice.Q1: How do I find a co-founder?Start by joining co-founder matching platforms like YC’s co-founder matching, university mailing lists, and local meetups. Often, friends or friends of friends are the best connections.Talk about what you're building on social media at least three times a week.When you find a promising partner, work on a small project together first to test compatibility.Join hackathons, take on side projects, or participate in school challenges to build experience.Investigate problems that you are uniquely positioned to work on.Develop a durable skill set, especially in building products in emerging markets like AI.Q2: How do I sell my first customers before my product is ready?This is a great opportunity to create a design partnership.Consider offering a mix of services and software to get started.If they truly need your solution, they will be patient—it’s a good test of urgency.Avoid endlessly delaying until you feel "ready"—perfection is a myth.Set a target date for release and keep them engaged along the way.Keep delivering value:Continue discovery—learn more about their specific needs.Provide access to prototypes and early versions.Offer no-cost pilots to keep them involved during final development stages.Q3: How do I hire my first salesperson?Seek advice from people who have hired salespeople before—they can guide you.Even if you don’t fully understand sales, great people can help you hire the right person.Ensure you’re actually ready—do you have a structured sales playbook to guide them?Write a clear sales playbook before hiring. If you can’t, you’re not ready yet.Post the job broadly to attract a wide range of candidates.Ask candidates to produce a sales deck or similar work sample as part of the screening process.Ash underscores how challenging it is to hire your first salesperson with this: hire three people, knowing that only one will likely be the right long-term fit.Tune into the full episode to learn how to navigate these challenging "getting started" moments!

In this episode we talk about process. Big companies have a lot of process, but startups have very little. How much process is enough for your startup? When do you have too little, or too much? We are here to help! In this episode we answer questions including:When is the right time to introduce process?What if an employee refuses to follow our processes?How do I know if we are using too much process?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.vcAsh Rust: Managing Partner, Sterling Road www.sterlingroad.comNic Meliones: CEO, Navi www.heynavi.comReminder: this is not legal advice or investment advice.Q1: When is the right time to introduce process?Too little process leads to chaos. Too much process slows you down. So how do you strike the right balance? The key is to avoid predictable failures – like running out of money, missing legal obligations, or failing to talk to enough customers. You should introduce process selectively to prevent these known risks.Some processes will naturally emerge as your startup grows. Instead of forcing structure too early, focus on where process adds real value, such as:- Goal setting (weekly, monthly, quarterly).- Standardized specs for software to maintain quality.- Clear rules for custom sales requests to avoid overpromising.The bottom line: don't create process for process's sake. Evolve it intentionally as your startup grows.Q2: What if a sales employee refuses to follow our processes?High performing salespeople often bend the rules. Should you let them? It depends.What really matters: are they selling the right value proposition? If they are delivering strong sales results without misleading customers or breaking pricing rules, flexibility can be beneficial.What's not OK: selling things that don't exist. Overpromising features. Ignoring pricing guidelines.How to handle it: give feedback and set clear boundaries. If you allow flexibility, let them know that you are basing it on performance. If the performance drops, that flexibility disappears.Bonus tip: you might actually learn from this sales employee! Great salespeople often find better ways to sell – listen and refine your processes accordingly.Q3: How do I know if we are using too much process?Warning signs:- Your velocity feels slow and your team struggles to keep up with opportunities.- Customers are moving faster than your product development.- You're spending more time on approvals and red tape than executing.The right amount of process should be invisible – it makes work easier, not harder. If process is slowing you down, cut back.A common trap: founders who hire product managers from large companies often end up with too much process. If your team feels like they are drowning in structure, it's time to simplify.

In this episode we talk about employee problems. If you have employees, some of them will create problems that you will have to solve. How do you solve employee problems without firing someone? When do you have to fire someone? We are here to help! In this episode we answer questions including:How do I handle an underperforming co-founder?What can I do about an employee who is chronically late?What if you suspect an employee has a second job?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.vcAsh Rust: Managing Partner, Sterling Road www.sterlingroad.comNic Meliones: CEO, Navi www.heynavi.comReminder: this is not legal advice or investment advice.Q1: How do I handle an underperforming co-founder?Here are our actionable tips:Weekly 1-on-1s are essential for resolving conflict and achieving alignment.Establish clear expectations for alignment and performance.Reflect on your own contributions to the problem: ask yourself, “what can I do better?”Seek coaching opportunities for your co-founder or explore if they might be a better fit in a different role.If you cannot achieve alignment with your co-founder, consider parting ways.Q2: What can I do about an employee who is chronically late?There are two distinct perspectives to consider:Flexibility is an advantage for your startup. Amazing talent with unorthodox work habits may unlock immense value for your startup.However, collaboration is key. The ability to collaborate is one of the most important skills someone needs in a startup. If punctuality impacts team dynamics, it is essential to address it.We had to settle this one through a tie-breaker decision! Be firm. Small adjustments are acceptable, but don’t compromise the ability to collaborate. All work is collaborative. Your team has to work together to achieve goals.Q3: What if you suspect an employee has a second job?1: Outcomes matter more than effort. Are they meeting their goals?2: Consider the cost of losing them vs. the value they bring to your startup.3: Reiterate that team meetings and collaborative efforts are non-negotiable.The key takeaway is this: ignoring problems sets a precedent that affects company culture. Company culture matters.