Strategies for Scaling a Startup Without Losing Focus

I’ve been the first marketer at two companies now worth over $2 billion. If I did it again, here’s 9 things I’d do differently: 1️⃣ Start with brand as a scalable system Build a modular design system early with components you can combine instead of create. A Figma system, Canva templates, Google Slide layouts. Pair that with a messaging doc, your "copy-paste" bank of positioning, beliefs, and product language. It becomes a foundation for consistency and a knowledge base for AI. 2️⃣ Prioritize the 95%, not just the 5% LinkedIn & search ads worked early, but only because we caught the 5% already in market. The "demand capture" pool dries up fast. Invest early in "demand creation." Reach the 95% who aren’t ready yet, but will be. 3️⃣ Build in public People trust people more than companies. Let internal voices share what they’re building and learning. In the AI era, content is easy. Opinion & stories are valuable. 4️⃣ Know your customer so well the strategy writes itself I used to sit on every sales call and write every piece of copy. That proximity helped me hear what customers cared about, what words they used, where they hung out. Be close enough to "hear the music," and messaging & growth channels become obvious. 5️⃣ Start community early Create spaces where early customers can connect: Slack, Reddit, meetups, certification. It fuels your roadmap and scales support when customers can help each other. Even better if it creates user-generated content that is indexable/shareable. 6️⃣ Create the problem Don’t build the whole funnel on day one. If you don’t have traffic, don’t worry about conversion. Solve the problem you actually have. Let the next one emerge or you'll be building and rebuilding as things inevitably change. 7️⃣ Look bigger than you are Design clean & consistent. Logo small (bigger companies don't oversize their logo). Feature your biggest customers, your compliance certifications. Use big company channels but use them small (buy one billboard, get one great PR story, speak on one well-known podcast). Make big company content but do it small (like a single high production video). 8️⃣ Build lightweight systems You don’t need full-blown infrastructure. A Notion board or copy-paste doc can carry you farther than you think. Build systems for speed, not scale. 9️⃣ Protect your focus Get used to working with an infinite backlog. I used to start each day with a sticky note on my laptop of my 3 to 5 most important tasks. You weren’t hired to do everything, you were hired to make impact. If you've done this - what would you add?

Growing a business requires a significant amount of strategic focus on acquiring new customers. Rolling out new products, expanding our target audience, and partnering with category-adjacent businesses are all critical strategies for scaling. However, an over emphasis on acquisition can often lead to losing sight of nurturing the people who've already chosen us. What's been on my mind lately is the real cost of falling into the "good enough" trap. While you're busy chasing new customers, another organization is working just as hard to win over yours. When complacency sets in, they're prepared to parachute in, make your customers feel like a priority, and communicate exactly what they can deliver to make them consider switching. Especially when consumers are increasingly price-conscious, scaling and growing your business isn't just an acquisition game. It's fundamentally about continually creating new ways to deliver value to your current customers. Here are some of my go-to approaches to deepen that connection and value with your existing audience: Predict and Reward: You have incredible data on what your customers do and want. Use it to stay one step ahead and deliver something that genuinely surprises them in the best way. Think proactive delight, not just reactive service. Build a Real Community: People crave belonging. They love being part of a group where they feel seen, heard, and valued. Whether it’s online spaces or in-person meetups, create a place where your customers can truly connect, share, and feel like they belong. That builds incredible stickiness. Go Above and Beyond: I had a shipping issue with a company recently, and they didn’t just fix it, they kept me updated every step of the way, apologized sincerely, and even provided extra products. It turned a momentary problem into a powerful moment of real trust and appreciation. We need to look at current customers differently. Instead of just viewing them as consistent buyers, we should see them as amplifiers, invaluable feedback providers, and crucial testers. They are often your strongest allies in scaling and growing your business because, when nurtured, they will grow with you.

If you’re feeling stretched too thin, wondering how long you can keep this up, you’re not alone. This week, I had a conversation with a CEO that stuck with me... We bonded over Pilates I was still in my gear when I showed up for our call (end-of-year grind mode with no breaks) She gave me grace, laughed it off, and within minutes blurted: “𝐻𝑜𝑤 𝑎𝑚 𝐼 𝑠𝑢𝑝𝑝𝑜𝑠𝑒𝑑 𝑡𝑜 𝑠𝑐𝑎𝑙𝑒 𝑡ℎ𝑖𝑠 𝑡ℎ𝑖𝑛𝑔 𝑤𝑖𝑡ℎ𝑜𝑢𝑡 𝑙𝑜𝑠𝑖𝑛𝑔 𝑚𝑦 𝑚𝑖𝑛𝑑?” That hit hard. I've had a variation of this conversation at least 15 times this week with busy execs trying to get everything done before 2025. She's a FORCE and running a multi-faceted startup. All the while closing enterprise deals while chasing unpaid invoices, trying to scale operations without breaking what's already working, and hiring a team that won't kill her company's scrappy, unique soul. If you’re a founder or CEO, chances are you’ve felt this tug-of-war: 𝐎𝐩𝐞𝐫𝐚𝐭𝐢𝐨𝐧𝐬: You know you need help, but every time you delegate, it feels like you’re trading execution for endless hand-holding. 𝐒𝐚𝐥𝐞𝐬: You’re torn between keeping big clients happy and building systems so revenue doesn’t depend entirely on you. 𝐓𝐞𝐚𝐦 𝐛𝐮𝐢𝐥𝐝𝐢𝐧𝐠: That last bad hire still stings, and now the stakes are higher. If “doing it all” was a viable strategy, we’d all have gold medals by now. It’s tempting to chase quick fixes, hire a unicorn, grab the latest tool, or outsource the mess. But without clarity on what you need and why, those solutions create expensive mistakes. 𝐓𝐡𝐢𝐬 𝐢𝐬 𝐭𝐡𝐞 𝐚𝐝𝐯𝐢𝐜𝐞 𝐈 𝐠𝐚𝐯𝐞 𝐡𝐞𝐫: 1️⃣ Stop hiring for titles Start hiring for the work that’s actually weighing you down. Get clear on what’s taking up your time. Are you spending hours tweaking content when you should be building investor relationships? Or stuck in ops fires when your focus should be strategic growth? 2️⃣ Timing is everything Hiring too soon, especially for leadership roles, creates chaos and kills the momentum you've worked so hard to build. Validate your systems and goals first. If you haven’t documented your process or pinpointed bottlenecks, handing it off will only magnify the problem. 3️⃣ Avoid shiny object syndrome It’s easy to fall for candidates with flashy profiles or big company experience you ultimately want to grow to be like. But they'll fizzle fast if they’re not ready to roll up their sleeves and do the work you need. As this vulnerable founder said, “𝐼 𝑗𝑢𝑠𝑡 𝑤𝑎𝑛𝑡 𝑠𝑜𝑚𝑒𝑜𝑛𝑒 𝑡𝑜 𝒐𝒘𝒏 𝑖𝑡.” I get it. But ownership only works when it’s clear what’s being handed over + the right time to hand it over. If you’re stretched between running the business and growing it, remember this: 𝐂𝐥𝐚𝐫𝐢𝐭𝐲 𝐢𝐬𝐧’𝐭 𝐚 𝐥𝐮𝐱𝐮𝐫𝐲, 𝐢𝐭’𝐬 𝐭𝐡𝐞 𝐟𝐨𝐮𝐧𝐝𝐚𝐭𝐢𝐨𝐧 𝐟𝐨𝐫 𝐬𝐮𝐬𝐭𝐚𝐢𝐧𝐚𝐛𝐥𝐞 𝐠𝐫𝐨𝐰𝐭𝐡. What’s the messiest part of your business that could use a Windex bottle and what’s the first step you’ll take to clean it up? #startups

"Do things that don't scale" is startup advice that ruins more founders than it helps. Month 1, you're manually onboarding users. Month 12, you're still doing it. Exhausted. No systems. Just grinding. That's not what Paul Graham (who said it) meant. We grew Gamma to 50M users with 28 people because we learned when to stop. Here's what nobody tells you about scaling: 1. Do the work yourself until patterns emerge GoPuff's student founders (Uber for munchies, delivering snacks and beer in 30 minutes) ran every delivery themselves for 4 months. 17-hour days, 7 days a week, sleeping and showering in the warehouse before morning classes. By month 4, they knew every late-night craving pattern by heart. Today: $15B valuation. The exhaustion has to teach you something, or you're just a masochist with a minivan. 2. Build communities to replace yourself Zoom's team was drowning in tickets after their 2020 explosion. They launched a community forum in 2021. By 2024, 150 volunteer "Community Champions" were answering >40% of all questions using the exact same language from Zoom's own docs. The volunteers knew the product better than some staff. 3. Turn repetitive pain into product features In 2009, Airbnb was dying: $200/week despite being in Y Combinator. Paul Graham: "Go meet your users." They flew to NYC and found the problem: every listing had terrible photos. Dark, blurry shots making nice apartments look sketchy. So they rented a camera and knocked on doors, shooting professional photos themselves. That week, revenue doubled. The photo runs became the Airbnb Photography Program, now thousands of photographers worldwide. Stuff that makes you want to bang your head against the wall: that's your product roadmap screaming at you. 4. Track the decay curve Your manual work should collapse, not creep upward. Bird hit $2B valuation while still relying on armies of gig workers roaming streets at 2am, stuffing scooters into minivans to charge at home. One charger earned $600 in a single night. The manual labor never shrank. They spent $3.60 to earn $1.00. Bird went public at $2.3B, then lost 96% of its value and filed Chapter 11. If your human-hours curve doesn't fall off a cliff, your market cap eventually will. 5. Know your graduation moment Every manual process has a clear endpoint: - When you can predict every question - When learning flatlines - When your community takes over Miss these signals and you're just moonlighting as customer success. —— Do unscalable things to learn ↓ Build systems from what you learned ↓ Get out of the way You're not grinding to be a hero. You're grinding to make yourself obsolete.

"Our competitor just raised $100M and launched our exact product." The founder looked defeated. But he didn't know he was about to win - by doing less, not more. While the bigger competitor was busy spending their $100M building everything for everyone, this founder did something counterintuitive: He went smaller. Focused on one customer segment that the big player was too busy to notice. The result? The funded competitor built 100 features My founder built 10, but they were exactly what his niche needed The competitor burned through cash trying to serve everyone My founder hit profitability serving just one vertical Now? The heavily funded competitor shut down after burning $180M. Meanwhile, the "small" startup is doing $50M ARR in their niche growing quickly. I've seen this pattern repeat for 15 years: Robinhood didn't try to be Charles Schwab Figma didn't try to be Adobe Notion didn't try to be Microsoft They each found their corner of the market and owned it completely. Here's what most founders miss: Startups rarely die because competitors are better or because they run out of money. They die because they lose focus trying to be better at everything instead of being the best at something. To founders: The next time a competitor raises a massive round, don't panic. Get more focused, not less. Your biggest threat isn't your competitor's bank account. It's losing sight of who you really serve. #StartupAdvice #VentureCapital #Entrepreneurship

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.