『The Startup Help Desk』のカバーアート

The Startup Help Desk

The Startup Help Desk

著者： Sean Byrnes Ash Rust & Nic Meliones
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Answers to your questions about starting and building companies. Your hosts are Sean Byrnes, Ash Rust and Nic Meliones, all experienced founders who have built companies themselves and coached hundreds of CEOs on their startup adventures. They share their lessons from building, buying, selling and investing in companies over the past 20 years. If you have questions you'd like answered you can submit them on Twitter by tagging @thestartuphd or on our website http://www.thestartuphelpdesk.com.

© 2026 The Startup Help Desk マネジメント・リーダーシップ リーダーシップ 経済学
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  • How Should I Spend My Startup's Money?

    How Should I Spend My Startup's Money?
    2026/09/14
    In this episode we talk about spending money. You have limited capital at a startup and you cannot afford to spend more than absolutely necessary. But what is necessary? When should you spend and when should you save? We are here to help! In this episode we answer questions including:How can you build spending discipline on your team?How do you know if the cost of tools are worth it?How should you approach expense policies?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: 2x Founder (writes https://meliones.substack.com/), Director of Implementation at Keebler Health.Reminder: this is not legal advice or investment advice.Q1: How can you build spending discipline on your team?"We raised a good round, but now the team seems to spend money too freely — expensive equipment, laptops, food, events. I worry we'll burn too much too fast. How do I reset spending habits?"Invert the question before you crack down. If you were near the end of your runway, what would you actually cut to survive? People and servers. Overspend rarely comes from laptops, food, or events. It comes from a team that got too big or server costs nobody turned off.Tie the fun things to outcomes instead of banning them. Upgrade the office equipment when you hit the growth milestone. Do the party at the great restaurant when you hit the next one. That resets expectations without turning you into the person who polices lunch.Every dollar you spend is a bet on speed. You raised money to move faster than the people trying to beat you. That's the frame: "does this buy us speed, and how will we know?"Money follows intent. Goals first, budget second. Work in reverse: name the goal, decide what it takes to motivate people toward it, then decide what spend serves that. And keep the receipt: check afterward whether the spend actually produced the result.Culture is set by what founders visibly do. You set the tone.Q2: How do you know if the cost of tools is worth it?"We keep spending more and more on AI tools, but I'm not seeing a rise in productivity. The team says these are 'must-have' tools in the current market. Shouldn't we see some obvious gains?"Yes. You should see gains, and you should see them almost immediately. Plenty of executives get hired, announce that they have to set everything up first, spend real money, and produce nothing two or three quarters later.Paying for a tool is not the same as using it well. "We implemented Salesforce" is not an achievement. It's a means to an end. If it shows up in your investor update as a win, something has gone wrong with how your team defines progress.Ignore the tools and look at the goals. Are they rising month over month, week over week? Are you hitting them? If spend is climbing and output isn't, you have your answer.Your team has a right to ask for the vendors and tools that help them hit a goal. Making them justify every line item is friction you don't need. What you owe them instead is high expectations.In 2026, if someone isn't compounding their output with this crop of AI tools – running large amounts of work concurrently – they may not be in that role by the end of the year. Give people what they need to adapt, and be honest that adapting is the job.Q3: How should you approach expense policies?"We don't have a formal expense policy – most of our employees know we're a startup. However, one does not, and expenses much more than the rest. I don't want to act like a big company. How do we keep this under control?""No policy" is a policy. It's just the wrong one. An expense policy is a must, and "we don't want to feel like a big company" is not a reason to skip it.The cost of no policy is paid by your most careful people. Lack of clarity slows things down and quietly hands privileges to whoever is comfortable assuming yes. Everyone else sits on the sideline with no idea what's allowed and expenses nothing. That's an unfair asymmetry you created by staying silent.Build your expense policy with your CPA. You can keep it to one page with four sections:What's clearly okayWhat's clearly not, with actual examplesWhen to ask firstHow to document an expenseDo it on day one. It saves mountains of headache later, and skipping it is effectively a bet that your company won't be around long enough for it to matter.Don't assume your hires arrive with good habits. Not everyone understands capital conservation, especially coming from a big company.Train the habits. Then enforce them. If someone is shown the line, given a fair chance to change, and keeps crossing it anyway, then this probably isn't the right place for them.
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    21 分
  • How Do I Handle Promotions?

    How Do I Handle Promotions?
    2026/07/24
    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 分
  • How Do I Build a Great Product Strategy?

    How Do I Build a Great Product Strategy?
    2025/12/17

    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 分
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