Episodes

  • How Do I Handle Promotions?

    How Do I Handle Promotions?
    Jul 24 2026
    In this episode we talk about promotions. You want to reward your best people by promoting them to new roles, but when and how? How can you avoid the dangers of bad promotions? We are here to help! In this episode we answer questions including:When should an individual contributor become a manager?How do you handle an employee that isn't growing with the business?What happens when two people vie for the same role?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, LucidFog www.lucidfog.comAsh Rust: Managing Partner, Sterling Road www.sterlingroad.comNic Meliones: Founder, Startup Coach https://meliones.substack.com/Reminder: this is not legal advice or investment advice.Q1: When should an individual contributor become a manager?"We have a great engineer who wants to become a manager. I don't think they'll be good at it or enjoy it, but we don't want to lose them. What can I do?"Promotions are bets on future performance, not rewards for past work. Wanting a great IC to keep producing is natural, but don't promote someone into a role you believe they'll fail at. Management is a different job, not a higher rung on the same ladder.Test the desire before you grant the title:Send them to a management training course. Five days of reports, emotion-management, and conflict-resolution role-play is a filter. It either kills the fantasy or proves they're serious. If they're serious, they'll learn the mechanics (1-on-1s, conflict resolution, the parts of the job nobody romanticizes) before they run a real team.Try a 50/50 split. Keep them contributing while they test-drive managing people. Low risk, high signal.Examine your own bias. Part of you wants the status quo: a great engineer shipping great work. But your job is also to serve their career. Ask what they actually want long-term. Often it isn't "manage people" – it's bigger scope, real decision-making authority, or more visibility. Answer that, and you frequently get more of what you want, too.Build a real IC path. Most people only chase management because they've been taught it's the only way forward. Show them ICs who've grown into the equivalent of VPs and the pressure to become a manager evaporates for the ones who never wanted it. Make being a senior IC as prestigious as being the boss.The trap: creatively forcing people into roles they don't fit. Architect real jobs that solve real company problems. Don't invent a "team lead" title for a team of one.Q2: How do you handle an employee that isn't growing with the business?"One of our earliest employees is great, but is quickly being left behind as the business grows. Their role is shrinking as the company grows. I'd hate to lose them — how can I help?"This happens at every fast-growing company. The job someone was hired for often doesn't exist six months later. Not everyone scales, and that's not a moral failing.Set expectations early and honestly, before it becomes a crisis. Tell the whole team, on a regular cadence: "The job you have today won't exist tomorrow. We'd love you to be first choice for the next one, but it's on you to show us." That conversation, held often, does more than any rescue attempt later.Invest, but keep a close eye on who is already pulling themselves forward. Coaching and training are worth trying. Importantly: people who scale are already training themselves, learning new skills, taking initiative. If you have to supply all the initiative to drag someone forward, it rarely works. You can only pull someone so far, and you shouldn't contort the whole org to meet one person where they are.Be honest that the odds are low. In most cases this ends with letting the person go. Give them a fair chance to find their place, but time is limited, and if they're not climbing this mountain, they're unlikely to climb the next one.The kindest move is often the exit. Help them find their next role. At a bigger company they may be iced out and miserable; as an early-stage specialist elsewhere, their zero-to-one strengths are a genuine asset.Watch where the pressure actually comes from. They may not feel it in the work, but they feel it interpersonally, early. The trigger is frequently the people underneath them: strong reports threatening to leave unless the blocker moves. That forces the hard conversation, and it's never comfortable to tell someone the team has outgrown them.Q3: What happens when two people vie for the same role?"I have two great salespeople who both want to become sales director. There's one opening, so I can promote one — but at the risk of losing the other. What should I do?"Don't assume your best AE becomes your best director. A great AE is a closer. A great sales director is a scaler: coaching, building process, designing the machine. Different job, different skill set. The ...
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    20 mins
  • How Do I Build a Great Product Strategy?

    How Do I Build a Great Product Strategy?
    Dec 17 2025

    In this episode we talk about product strategy. How do you make sure your product wins in the market? How do you make key product decisions, and how do you manage mistakes? We are here to help! In this episode we answer questions including:

    • What do you do when big feature releases fail to move the needle?
    • How do you balance different requests from different customers?
    • What's the best way to communicate product roadmaps?

    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.
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    21 mins
  • How do VC firms work?

    How do VC firms work?
    Dec 4 2025

    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.

    The Golden Rule: Every single check a VC writes must have the theoretical potential to return the entire fund on its own.
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    25 mins
  • What is the Secret to Faster Growth?

    What is the Secret to Faster Growth?
    Oct 16 2025

    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.
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    23 mins
  • How Should You Structure Your Team?

    How Should You Structure Your Team?
    Sep 26 2025

    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.
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    23 mins
  • Should You Raise Strategic Financing?

    Should You Raise Strategic Financing?
    Jul 25 2025

    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.
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    21 mins
  • How to Navigate Co-founder Relationships?

    How to Navigate Co-founder Relationships?
    Jul 10 2025

    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.
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    20 mins
  • Tales from the Trenches

    Tales from the Trenches
    Jun 30 2025

    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.
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    35 mins