How to Scale as an Early Stage Founder

Only 8% of startups hit $10M+ with under 10 employees. Most of them fail, not because the product is bad. But the operations collapse before scale ever becomes sustainable. There’s a reason most early-stage startups stall at the $1–3M ceiling. It’s not product. It’s not marketing. It’s operational entropy disguised as scale. Too many founders optimize for growth at the expense of throughput, margin fidelity, and execution per head. According to the 2024 Indie.vc + MicroConf report, only 8% of startups that cross $10M ARR do it with fewer than 10 full-time employees. That stat tells a bigger story, most teams are bloated before they’re functional. They raise pre-seed, stack 7 FTEs, and add “leadership” before product loops are even validated. I’ve built and exited one of those rare companies: $100M+ revenue, zero outside capital. We ran clean, margin-led, and headcount-disciplined. Here’s what I tell founders now, whether they’re bootstrapped or post-seed: 1. Don’t hire functions. Scale throughput. Startup headcount should be attached to repeatable economic motion—not a department slide. → Audit for repeatable customer acquisition channels → Break that into unit economics → Assign throughput targets before job descriptions Until the loop is reliable, the hire is overhead. 2. Treat every FTE as dilution, even if you’re bootstrapped. Most founders ignore this, but every hire even bootstrapped is a form of equity cost. → Will this hire compress EBITDA? → Will it extend your payback window? → Will it increase burn without increasing velocity? I use this internal filter with every portfolio founder: “Would you add this headcount if it meant taking 5% off your personal equity at exit?” If the answer’s no, you’re not hiring for leverage. You’re hiring for comfort. 3. Design internal motion before adding external complexity. Most startups are tactically overloaded but strategically hollow. They chase “what works” for other startups and bolt on layers they can’t support. I always ask: → Do you have a weekly execution loop owned by a human—not a dashboard? → Do you have functional accountability by output, not title? → Do you know your marginal ROI per additional head? If not, adding people will only spread the mess wider. High-growth companies don’t scale because of speed. They scale because of internal simplicity. This is where lean shines. It forces clarity, kills ornamental hiring.and surfaces the brutal truth about who on your team actually moves the needle. One of the best operators I know said this to me last year: “I don’t track revenue per employee. I track speed per employee.” Before you add another salary, ask yourself: → Can I run this through a profit lens? → Will this hire increase velocity per dollar—or just give me breathing room?” In early-stage, you’re not building culture. You’re building throughput. Optimize accordingly. #Founders #systems #startups #bootstrapping #entrepreneurship

You'll never "feel" ready to scale your company. That's where most founders get stuck. They wait for readiness to happen: - The product to be "perfect" - The team to be "fully staffed" - The systems to feel "strong enough" But here's the hard reality I've learned working with 50+ scaling companies: scaling isn't something you ease into. It's something you decide to do. Founders who wait to "feel ready" never do. They wait. They stall. And they get outpaced by companies who made the call to scale before they felt comfortable. I see this pattern every week: 🚨 Stuck founders... - Binge "growth hacks" - Throw $50K/month at ads - Panic-hire 3-4 salespeople And yes, it works... For about a quarter. Then reality hits: → Tech debt balloons 300% → Customer satisfaction drops 40% → Server crashes during peak traffic → Manual processes collapse under load → Growth transforms into expensive churn The real move isn't waiting until you feel ready... or trying to duct tape growth with marketing spend. The only way to scale without breaking your company is getting your tech infrastructure ahead of your ambition. Here's what actually works: 1. Decide to scale 2. Build to handle it 3. Then hit the gas As a fractional CIO, I just helped a SaaS client go from 500 to 2,000 users in six months. The difference between their success and others I've seen struggle? They built the foundation first. Before the growth surge, we: → Automated their customer onboarding (reduced manual work by 80%) → Implemented proper database architecture (eliminated those 3am "server down" calls) → Set up monitoring and alerts (caught issues before customers did) That means professionalizing your: → Systems (before they break under load) → Processes (before bottlenecks cripple momentum) → Tech stack (before technical debt suffocates growth) I've seen companies go from $1M to $10M in 18 months using this approach. And I've watched others stall at $2M for years waiting to "feel ready." It's not about feelings. It's about decisions and strategic preparation. Standing at that line between founder-led startup and scalable business? Don't wait for a feeling. Decide. What's your biggest tech bottleneck right now? Let me know below 👇

From Vision to Execution: Early Lessons working with Start-ups    Over the past year, I’ve had the privilege of working with several early-stage companies in the healthcare, AI, and education sectors. It’s been a lot of fun — but let’s be honest, leading an early-stage company is a tough job. The founders and leaders I’ve worked with have incredible vision. Their ideas resonate, customers are coming on board, and capital is starting to flow. That early traction is exciting — and it should be celebrated. But this is also where the real struggles begin. Turning a brilliant idea into a sustainable business requires a different skill set. The creativity that fuels the start-up phase now also needs discipline, structure, and the ability to make trade-offs. Here are four things I’ve observed that might help: 1)    Start your board early and focus on building one that genuinely adds value. A good board is more than governance; it’s leverage. The right members open doors to customers, investors, and partners; they lend credibility; and they help shape strategy with the benefit of experience. Think early about what relationships, expertise, and perspective your company needs, and build your board with purpose. 2)    Hire for the stage you’re in, or about to go in. Your team thrived in the idea stage, but they may not be the team that will thrive during the ramp-up and execution stage. The challenges you may now face—data privacy, compliance, regulatory, or financial—may call for individuals with experience in these areas. Ask yourself: What are the biggest execution challenges ahead, and do I have the right people in place to meet them? 3)    Get the fundamentals in order—investors notice. The companies I’ve worked with are so focused on the ‘exciting stuff’ that the boring ‘governance stuff’ gets overlooked. Credibility with investors comes from the basics: clean equity tables, visibility on burn rate, sound financial models, and transparent structures. These aren’t just “nice to haves” — they’re the hygiene factors that let investors focus on your growth story rather than questioning your foundations. 4)    Plan your runway You can’t do everything with the money you have currently, so you need to make the right choices and trade-offs.  Map your burn rate against key milestones and know what needs to be achieved before the next raise. Be disciplined in your planning. Scaling a start-up isn’t easy, but here’s where the opportunity lies.  By focusing on building the discipline, the team, and the choices that turn good ideas into lasting businesses, founders and leaders can make a difference.   

Most founders never break $10m. Not because they aren’t smart or hardworking. They just don’t know how to scale. I took AppSumo from $3m to $84m in six years. Bootstrapped. Here’s the exact framework I used to do it: ~~ Before we dive in—this post is just a preview. I broke down these frameworks in depth with Greg Isenberg on his podcast. I'll share the link to watch in the comments. == 1. The "9 Steps to 9 Figures" Framework Scaling happens in three phases: • Startup ($0-$1M): Find product-market fit. • Scale-up ($1M-$100M): Build a machine. • Grow-up ($100M+): Protect the legacy. Each phase requires a different skillset, mindset, and strategy. == 2. The Triple, Triple, Double, Double Formula Triple your business three years in a row. Double your business twice in a row. Here’s is the roadmap: Year 1: $1M → $3M Year 2: $3M → $9M Year 3: $9M → $27M Year 4: $27M → $54M Year 5: $54M → $108M == 3. Find Product-Market Fit first You don’t have product-market fit until it feels like you're wearing a meat suit in a dog park. If you’re still convincing customers to buy, you aren’t there yet. When you can’t keep up with demand, now you’re scaling. == 4. Retention before growth Building a business without fixing churn is like building a skyscraper on sand. Every 3% increase in net revenue retention DOUBLES your company’s valuation. Before you scale, fix retention. Otherwise, you’re filling a leaky bucket. == 5. The 80/20 Growth Rule • 80% of your resources on what’s already working. • 20% on new experiments. At AppSumo, one small test—switching from credits to cash payments for referrals—became an 8-figure revenue channel. Test small. Scale what works. == 6. You only have two bottlenecks If you're stuck, your problem is either: • Sales – Not enough leads? You don’t have a marketing problem. You have a product problem. • Delivery – Selling more than you can fulfill? You’re scaling chaos, not a business. Fix these first. == 7. Hire to scale revenue, not to discover it. Most founders hire too soon. Your job is to find the gold vein. Your team’s job is to mine it. Hiring too early = You burn cash. Hiring too late = You burn out. Hire only when scaling becomes the bottleneck. == 8. The Shield vs. Sword Framework for decision-making Rate every decision 1-5 on: • Impact (Sword) – How big is the upside? • Effort (Shield) – How much work is it? Only pursue 8+/10 ideas. If it’s not a clear win, it’s a distraction. == 9. Build an executive team that replaces you Your business only has two core functions: • Sales (CRO) – Gets Customers • Delivery (COO) – Keeps Customers Pro tip: Hire first in your zone of genius. Why? Because you’ll know what excellence looks like. == 10. The founder is the hardest worker. The CEO is the laziest. If your calendar is full, you're still a founder. A CEO’s job is to think 3-5 quarters ahead while the team executes. If you’re in meetings all day, you aren’t running the company.

The hardest lesson I learned as a founder? Letting go. It's about trust. I used to micromanage every event detail. Now, I focus on empowering my team. I want a team-managed company. To scale, you have to let go and empower your team. They will make mistakes along the way, it's part of the process. Here's how: 1. Clear expectations: Define success upfront. 2. Right person, right task: Match skills to challenges. 3. Regular check-ins: Guide, don't hover. 4. Feedback loop: Encourage open communication. 5. Celebrate wins: Recognize team efforts. The result? Creativity flourished. Team morale soared. Our events got better. Quality control shifted from policing to mentoring. We built systems, not restrictions. I focus on vision and strategy. My team handles execution. They surprise me daily with their ingenuity. Founders, your job isn't to do everything. It's to build a team that can. #leadership #Innovation #BusinessExcellence

Scaling doesn’t mean doing more. It means building something that runs better with less of you. This took me a long time to accept. In the early days, I believed growth came from force. More time. More output. More effort. If I worked harder, I thought everything would grow. It did work for a while But eventually, it broke Because true scale doesn’t come from working more It comes from building smarter Here’s how I see the journey now You start by selling your time Then your process Then your system Eventually, your method and brand carry the weight Every stage forces change In how you think In what you prioritize In how you lead I used to do it all Close every deal Deliver everything myself Rely on a few star players Post content when I had time Hire when I was already overwhelmed None of it was sustainable And it definitely wasn’t scalable So I made the shift I turned custom work into repeatable delivery I created playbooks before handing off tasks I built a real content engine I set up systems to run without me I mapped out team needs before they became urgent These decisions made space Space to breathe Space to lead Space to grow If your business still needs you every day It isn’t scaling It’s just surviving Real growth means letting go of control So you can build something that stands without you #Growth #Systems #Strategy

That’s what it feels like for most founders. 👇   And the common advice?   Hustle harder.   But hustle alone won’t get you to scale.   At Grasshopper, we hustled hard in the beginning — constant problem-solving and working insane hours.   But that was never going to get us from $0 to $30M ARR.   What made the real difference? We built systems that did the heavy lifting for us.   That’s how we bootstrapped Grasshopper, scaled it to tens of millions in revenue, and sold it to Citrix — all without outside funding.   Hustle will get you through the early days. But if you’re still grinding the same way years later, ask yourself:   "Am I building a business that works for me or one that only works if I do?"   Founder-led growth does not mean doing everything yourself forever.   It’s not about being the hardest worker in the room or making every decision. That’s a recipe for burnout, not scale.   Because no matter how fast you run, the treadmill never stops.   So what to do?   → Convert hustle energy into system thinking.   A founder’s instinct is to push harder. Turn that drive into optimizing systems instead of hands-on work.   Ask: “Where am I the bottleneck, and how do I remove myself without losing control?”   → Stop thinking in terms of addition; start thinking in terms of multiplication.   Ask: “How can I get 10x results without adding more hours?”   Leverage automation, delegation, and compounding advantages like brand equity and repeatable revenue streams.   → Build a business that can grow — and sell — without you.   Even if you don’t plan to sell, your company should be valuable beyond your direct involvement.   If the business only works because you do, then you don’t own a business. You own a job.   → Also, rest.   Sometimes, founders forget that.

If I could give startup founders one piece of advice, this is what it would be: Don’t wait until you need to scale to get the right tools for scale. I’ve seen this play out too often: You’re scaling fast — more jobs, more people, more risk — and your systems just don’t keep up. The symptoms show up everywhere: In bloated inboxes, 20-minute quality checks, a hundred “where’s my order?” calls... And by the time you identify the problem, you’ve missed the growth opportunity. This does not have to be your story. Take Facility Solutions Group (FSG) as an example. Thousands of employees, over a thousand vendors, and a prefab operation expanding at full speed. All held together by tools that didn’t talk to each other. “I was using Google Sheets, Gmail, texts, calls—everything,” said Nathaniel Kevresian, FSG’s Prefab Manager. “I felt scattered.” That’s when Nathaniel did something I admire. He didn’t wait for an off-the-shelf fix. He used Quickbase to build a solution for how his team actually works. ↳ Job orders now live in real-time dashboards  ↳ QA/QC forms get done 20 minutes faster  ↳ Labor, inventory, and build progress are all connected  ↳ Everyone, even apprentices, are looped in and listened to Scale doesn’t have to start when you hit $50M in revenue. It can start the moment your tech gets out of the way of your process. The sooner you build systems that flex with your team, the more room you create for real growth. FSG didn’t wait to break. They built to move faster, listen better, and lead smarter. And that’s what separates the companies that stall from the ones that scale. 

Breaking news: your business won’t scale if you keep nibbling on morsels. In 2010, e-Nor was an established Google Partner in web analytics. But with the rise of smartphones, mobile analytics was the new kid on the block. One Friday, a $𝟱𝟬𝟬𝗠 video streaming company reached out—they needed mobile analytics. My co-founder 𝗿𝗲𝗳𝘂𝘀𝗲𝗱 to sell to them: "𝘞𝘦 𝘩𝘢𝘷𝘦𝘯’𝘵 𝘥𝘰𝘯𝘦 𝘮𝘰𝘣𝘪𝘭𝘦 𝘺𝘦𝘵." But I wasn’t about to let this wave pass us. We immediately looked for an app to play with and spent the entire weekend running tests. On Monday, I responded to the lead, “𝘞𝘦’𝘷𝘦 𝘥𝘰𝘯𝘦 𝘵𝘩𝘪𝘴 𝘣𝘦𝘧𝘰𝘳𝘦.” A few months later, we delivered the project, the client was happy, and we made $30K. More importantly, we went on to build a dedicated mobile practice and worked with some of the world’s biggest brands. 𝗦𝗰𝗮𝗹𝗶𝗻𝗴 𝗶𝘀𝗻’𝘁 𝗮𝗯𝗼𝘂𝘁 𝘄𝗮𝗶𝘁𝗶𝗻𝗴 𝘂𝗻𝘁𝗶𝗹 𝘆𝗼𝘂’𝗿𝗲 𝟭𝟬𝟬% 𝗿𝗲𝗮𝗱𝘆. 𝗜𝘁’𝘀 𝗮𝗯𝗼𝘂𝘁 𝘁𝗮𝗸𝗶𝗻𝗴 𝗰𝗮𝗹𝗰𝘂𝗹𝗮𝘁𝗲𝗱 𝗿𝗶𝘀𝗸𝘀. If an opportunity feels "too big," 𝗱𝗼𝗻’𝘁 𝗶𝗺𝗺𝗲𝗱𝗶𝗮𝘁𝗲𝗹𝘆 𝘁𝘂𝗿𝗻 𝗶𝘁 𝗱𝗼𝘄𝗻: 1. Assess the learning curve. Can you push yourself to meet the demand? 2. Buy time. Extend the sales cycle to research and prepare. 3. Leverage external expertise. Subcontract what you can’t do yet. 𝗥𝘂𝗻 𝘁𝗵𝗶𝘀 𝘁𝗲𝘀𝘁: • Learning curve: low/high • Sales cycle: short/long • Delivery timeline: tight/flexible • Access to expert help: limited/abundant If only 1-2 are "low," go for it. If 3 are "low," negotiate more time. If all 4 are "low," pass for now. Bottom line: Stop feeding on scraps. Follow me for insights on increasing your margins. #entrepreneurship

🚨🚨🚨 Founders! Learning and scaling are two different things! I recently had a board meeting with a brilliant portfolio founder and we had a fantastic discussion on the differences between being in “learning” mode and “scaling” mode. We discussed how far too often the word “scaling” is thrown around so loosely, especially within the context of a venture backed business. At the pre-seed and seed stage it is super important to be laser focused on learning as much as you can about the end customer, the pain point, purchasing, usage, product build out, and so on. Although you can technically balance the art of learning and scaling (and the best companies who ultimately achieve PMF do this in perpetuity), when you’re early on and resourcing is tight it is *very important* to be self aware and make sure you don’t rush the “learning phase” of company / product development. Scaling involves a particular mentality and use of resourcing and typically results in learning taking a back seat. The temptation to press on the pedal and “accelerate” is very real, especially when VCs are investing millions of dollars into your business and the “narrative for scale” is what they want to hear. Be sure to master your own metrics, understand what works vs doesn’t work, become comfortable with moving at your own pace, and be VERY weary of vanity metrics. There will be a time and place for “scaling”. After all, a company’s scaling is only as good as how obsessed their end customers are with the product & services provided by said company– and this last part can only be achieved with ample learning.