Startup Case Studies and Lessons Learned

My startup pivoted 6 times before we landed on an idea that got us to PMF (signal-based sales platform for Demand Gen). In the beginning, here are 6 lessons I wish I knew: 1 - On Pivoting: alternate between open and closed periods Most founder say say, 'We're going to try this new idea, but we're not going to get rid of the old idea'... Instead do an open period of exploration for 30 days. Any idea works. Then pick one. Then do a closed period. Start with 30 days. You're ONLY allowed to work on that one idea. If a new idea comes in? write it down on a doc titled "ideas to return to during open period" After 30 days you can decide: do we continue in a closed period or return to an open period. Then repeat but make the closed periods longer and longer (60 days, 100 days, 1 year). Dedicate specific periods to exploration, then commit entirely to execution for increasingly longer intervals. 2 - On Co-Founders: talk to your co-founders daily If I'm not going back and forth, seven days a week, 365 days a year, with my co-founders, we're not moving the chains in the business. This level of communication is non-negotiable for alignment and rapid progress. 3 - On Decisions: choose whatever makes you $$ the fastest Whenever a team member proposes an idea to me I say "Tell me a story that starts with your idea and ends with us making more money, and make that story as short as possible." The fewer steps between idea and revenue, the better. 4 - On Focus: cut what doesn't fit I made the tough decision to fire 11% of our customers last year when we moved up market and they weren't ICP. This freed resources and focus to better serve our ideal customers. You can cut lots of projects/focuses in your startup without missing out much. 5 - On Personal Speed: embrace necessary discomfort When things aren't going well, resist the urge to focus only on what you're good at, and instead address the fundamental issues. If things suck and you're an engineer - you will code because you're good at it If things suck and you're a seller - you will sell because you're good at it But if things suck you can't get out of it by doing what you do best. Don't do the things that make you comfortable, because you'll fail if you do. Engineers go sell. Sellers go to product/customer discovery. 6 - On Company Speed: build learning into your culture One of our core values at Warmly is "slope > Y-intercept" – we prefer team members who learn quickly over those who start with more knowledge but grow more slowly. It's kind of a math nerd thing but slope is your rate of change. Y-intercept is where you start. Whoever has the highest rate of change (aka learning) will always win over time no matter who has the higher start. I've seen new grads run laps around enterprise sellers in 18 months because they were savages. Put speed of learning into your company. #founder #startup

A friend of mine just told me they’re winding down their startup after 6 years. They raised $80M from top-tier investors and had Fortune 100 customers. The shutdown isn’t due to fraud or a bad market. It’s something more common—and more preventable. He asked me to share this with other founders. The biggest mistake? Optimizing for speed and perception, not sustainability. In year 2, they landed a massive strategic partnership. It wasn’t profitable, but it brought validation and press. The narrative looked incredible. That momentum drove their Series B—$40M at a sky-high valuation. Here’s what went wrong: • The product was still duct tape and dreams. • The economics didn’t scale. • The team was young and learning in real-time. But the valuation assumed they were a rocketship. So they had to keep behaving like one—growing headcount, burning fast, chasing “hypergrowth.” They were on a treadmill they couldn’t get off. If they slowed, investors would panic. If they kept going, they’d run out of cash. Eventually, the growth slowed. Retention dropped. Customers churned. Follow-on investors passed. They were too big to be scrappy and too early to be efficient. And they didn’t have time to fix it. ⸻ The lesson? Startups don’t die from lack of ambition. They die from indegestion. Raising a big round doesn’t make you a big company. Don’t sprint to prove a story that isn’t ready. Build the fundamentals. Test the core assumptions. Stay in control of your burn. And above all—don’t let vanity metrics define your trajectory. You only get to scale once. Make sure you’re actually ready.

Startup Shutdown: After 6 months of building, we’ve decided to shut down our soccer-tech product, Lighthouse. It didn’t turn into the business we hoped for, but the lessons were real. Here are a few that stand out: 1. Too many pros, too soon. We onboarded 50+ soccer pros quickly—but didn’t activate or support them consistently. If I could do it again, I’d start with 5–10 and dial in the experience before scaling. 2. One thing at a time. Trying to build a marketplace and launch a youth soccer club was too much. We should’ve stayed focused on just the tech. 3. Keep the team smaller, longer. We capped headcount at 5, but even that was too much too soon. Gregory and I should’ve stuck to just the two of us until real traction. That’s the plan with our next startup, Velora.mvp. 4. Video content is an unfair advantage. This was my first time building a startup with a modest TikTok and IG following. The firehose of interest from day 1 from users, partners, and investors was unlike anything I’ve seen. What used to take 2 years to build through ads, PR, and word of mouth can now happen in 90 days with short-form video. With that constant inbound, you can rapidly test new product or business model changes—and know almost overnight whether you're building something people actually care about. 5. Soccer pros in the US are incredible to work with. Even with bugs and half-baked features, the pros stayed super engaged. They were patient, mission-driven, and eager to support the next generation. We made some mistakes—but I’m pretty sure even a perfect execution wouldn’t have changed the outcome. I’m super grateful for the experience—and excited for the next!

Canva and Lucidpress started with the exact same insight. One became a $40B company. The other pivoted away. I saw this play out firsthand as Head of Marketing at Lucidpress, where I spent six years leading our go-to-market strategy. Here's what we both knew: non-designers needed help creating beautiful designs. But that's where our paths diverged dramatically. Here's what we did: → Built features for multiple use cases → Created messaging for different personas → Spread ourselves across various channels → Tried to please everyone who showed interest Meanwhile, Canva was ruthlessly focused. They took that same insight and turned it into their entire strategy: → Every feature solved that core problem → All messaging spoke to that pain point → SEO/search was their primary channel → They dominated where these users looked for help The result? They became a $40B company. We eventually pivoted to a different market entirely (and I led that repositioning). Here's what I learned about GTM strategy: → Having a clear insight isn't enough → Success comes from ruthless focus on that insight Why is this so hard? Because saying no feels like leaving money on the table. Every new feature request seems urgent. Every potential customer segment looks promising. Every marketing channel appears worth testing. But the companies that win aren't the ones that chase every opportunity. They're the ones with the discipline to stay focused on one clear vision. This lesson fundamentally changed how I approach go-to-market strategy today. Hindsight is 20/20, but man, what a lesson. #startup #marketing

I’ve been building my startup - Dock - for three years. We now have 250 paying customers and have closed more revenue this year than all the previous years combined. Here are five company-building lessons I’ve learned along the way: 1) Founder relationships are crucial The founding group - Victor, Luc, and myself - are the heartbeat of the organization. Our relationship works because we have complimentary skills. We’re experts in our own fields (engineering, design, and GTM) and trust each other to make decisions. Above all else, having people in the trenches alongside you makes it easier to navigate the ups & downs of building a startup. 2) Hybrid organizations are the future Dock started as a fully remote company, allowing us to access incredible talent from all over the world. Over time, we’ve drifted to a hybrid organization with a small office in San Francisco. I’ve found that in-person time has been critical to our success. We’re able to discuss complex product decisions that would have been impossible over Zoom. It’s also easier to focus on work in an office without the distractions of home life. 3) Iteration is key to building successful startups  We've made many mistakes while building Dock. We tried to be fully product-led and started to build a product that solved too many problems for too many people. The list goes on. However, through daily iteration, we've transformed Dock into a successful product. We narrowed our focus to revenue teams, rebuilt features until we got them right, and changed our GTM motion to be more sales-led. Your success is determined by how quickly you learn from your mistakes. 4) Amazing hires drive growth Dock's growth has been propelled by the talented people we've hired. Joey transformed our sales motion. Madison has elevated our customer onboarding and support. Eric has built an inbound machine. Arpit and Segun have developed key features that our customers use daily. I wish I could mention everyone at Dock because each person's contribution is significant. By hiring exceptional people, I've been able to focus on my strengths - building an awesome (and useful) product and spreading the word about Dock. Since expanding the team, our revenue has tripled. 5) Startups require patience Building great software takes time. Customers have high expectations and won't settle for a subpar MVP solution. You need to build high-quality software that solves a unique problem for your customers. This is an iterative process of building, collecting feedback, and refining. When you're in the middle of this process, progress can feel slow, but the work compounds over time. This happens with both the product and the GTM side of things. You start to build a brand, refine your sales process, and improve SEO. Suddenly, you begin to see tangible progress and revenue increases. The past three years have been a challenging, but rewarding experience. There’s nothing better than building something that people love.

In 8 years, Pavilion went from a local happy hour for 10 overworked VP of Sales to a global platform with 10,000 paying members around the world. Here are the 5 biggest lessons I learned about growing a startup: 1. Focus Your market is bigger than you think. Your first group of products will scale further than you think. Before $20M in ARR, resist the temptation to go broad.  Resist the temptation to open an office in a new geo. Resist the temptation to sell to an adjacent customer. Every new initiative or GTM motion is costly, time consuming and distracting. You’ll need all of those things eventually (new markets, new customers, new products), just not as soon as you think. Enjoy the beautiful monotony of doing one thing very well. 2. Talent drives outcomes Your execution is directly related to the quality of talent on your team.  You want there to be a mix of people that are hungry and can learn.  And you want there to be people with deep subject matter expertise.  But understand that your results are going to be driven by the quality of the “motor” from the people on your team.  Lower you hiring standards at your peril.  It will show up in slipping targets and missed forecasts. The old adage “hire slowly, fire quickly" is true.  Hiring for a role out of desperation is a surefire path to mediocrity.  3. Never lose sight of the customer Your customers will provide you the roadmap. In B2B especially, you’re not Steve Jobs.  You don’t need to know better than them. Avoid drawing up your strategy in a backroom whiteboard without checking in with them. Avoid product teams that don’t spend time deeply interacting with customers. Avoid zooming out so far you lose empathy for what motivates them. Customers are your north star.  4. Size your bets For most questions, it’s not “if” you should do something but to what extent.  New ideas should be encouraged but preserve your precious capital by ensuring that before you go big you have enough data to understand HOW big.  Maybe you should build a new GTM motion but that doesn’t mean throwing millions of $$$ at that new motion before you have evidence it works. 3 AE’s hitting quota? Great! That doesn’t mean hire 20. Hire 3 more. See how they do. Channels don’t scale linearly. Size your bets. 5. Build your operating rhythm Every company needs an operating system. Ideas are great. Talent is great.  But you need a system where the team is reviewing performance on a regular basis, is accountable to each other, understands expectations, and feels pressure to deliver results.  So figure out what your system should be. It can be V2MOM. It can be EOS.  But it has to be something that provides a rhythm to your team and builds discipline and a regular reporting cadence. Bottom line... The most important lesson is the first one: Focus.  Get GREAT at a small number of things. Not good at a huge number of things Being great is 10x the value of being good.

I took my AI startup from 0 to Y Combinator acceptance, only to watch it collapse a few days before joining the program. Nothing prepared me for startup life - not my previous roles, not my side hustles, not my founder friends, not podcasts or books. The path from zero to one was harder and more lonely than I imagined, especially as a solo founder initially. If I had to do it again, here are the 5 critical lessons I learned the hard way. 1. Co-founder chemistry isn't enough. My co-founder quit before we could join YC S23, despite our initial alignment. The very first question you should ask: "Would they start a company without me?" True commitment comes from within, especially when times get tough. 2. Technology ≠ Solution. We built a cool AI tool that hit 30K monthly users but had poor retention. We were so focused on applying GenAI that we forgot to solve actual problems users cared about. 3. Not all problems are worth solving. We chased problems that weren't "hair on fire" urgent. Users kept asking for more features to justify adoption - a clear sign we weren't addressing something critical. 4. Customer selection matters enormously. We built for enterprises that required security infrastructure we couldn't deliver as a startup. In retrospect, we should have started with smaller, more agile customers. 5. Structure beats enthusiasm. The customer discovery process we eventually developed (clear hypotheses, minimum viable tests, consistent interview frameworks) should have been our day one approach. Despite the failure, we did some things right - launching five validation sprints, shipping two products that reached 25K+ combined MAUs, and getting accepted to YC S23 (even though we couldn't attend). This was the first real failure of my career, and it stung. But it's made me a better product person, a better founder, and honestly, a better human.

23andMe raised $850M+, $6B valuation, and went public. → but funding can't fix a broken business model What happened? And what can founders learn? Remember when 23andMe was the darling of biotech? Today? Bankrupt. So, what went wrong? More importantly, what can founders learn? 1. 𝗢𝗻𝗲-𝗧𝗶𝗺𝗲 𝗥𝗲𝘃𝗲𝗻𝘂𝗲 𝗠𝗼𝗱𝗲𝗹𝘀 𝗔𝗿𝗲 𝗮 𝗧𝗿𝗮𝗽 Selling DNA kits was great—until they ran out of new customers. No strong recurring revenue = financial struggle. 𝗟𝗲𝘀𝘀𝗼𝗻: If your model is based on one-time sales, you better have a killer plan for repeat business. 2. 𝗗𝗮𝘁𝗮 𝗣𝗿𝗶𝘃𝗮𝗰𝘆 𝗔𝗶𝗻’𝘁 𝗢𝗽𝘁𝗶𝗼𝗻𝗮𝗹 23andMe suffered a huge data breach in 2023, exposing nearly 7M users’ personal info. In a business where trust is everything, that’s a death sentence. 𝗟𝗲𝘀𝘀𝗼𝗻: If your business depends on sensitive data, security isn’t a feature—it’s survival. 3. 𝗖𝗮𝗽𝗶𝘁𝗮𝗹 ≠ 𝗦𝘂𝗰𝗰𝗲𝘀𝘀 They raised almost a billion dollars and still collapsed. Why? Because funding can’t fix a broken business model. 𝗟𝗲𝘀𝘀𝗼𝗻: Fundraising isn’t the goal—profitability is. If your business needs endless cash to survive, it’s not a business. 4. 𝗗𝗶𝘀𝗿𝘂𝗽𝘁𝗶𝗼𝗻 𝗪𝗶𝘁𝗵𝗼𝘂𝘁 𝗮 𝗕𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝗠𝗼𝗱𝗲𝗹 𝗜𝘀 𝗝𝘂𝘀𝘁 𝗡𝗼𝗶𝘀𝗲 23andMe disrupted the DNA testing industry but never figured out how to make the business work long-term. They pivoted into pharma partnerships, drug discovery, telehealth… but none of it stuck. 𝗟𝗲𝘀𝘀𝗼𝗻: Pivots should be strategic, not desperate. 5. 𝗜𝗳 𝗬𝗼𝘂’𝗿𝗲 𝗡𝗼𝘁 𝘁𝗵𝗲 𝗕𝘂𝘆𝗲𝗿, 𝗬𝗼𝘂’𝗿𝗲 𝘁𝗵𝗲 𝗣𝗿𝗼𝗱𝘂𝗰𝘁 They monetized user data for pharma deals—legally. But when customers realized they weren’t the customer, but the product? Trust plummeted. 𝗟𝗲𝘀𝘀𝗼𝗻: If your real business model is selling data, be transparent—or expect backlash. 6. 𝗔 𝗕𝗶𝗴 𝗘𝘅𝗶𝘁 ≠ 𝗔 𝗕𝗶𝗴 𝗦𝘂𝗰𝗰𝗲𝘀𝘀 They went public via SPAC at a $3.5B valuation—only to end up bankrupt. 𝗟𝗲𝘀𝘀𝗼𝗻: Going public isn’t the finish line. If your fundamentals are weak, it’s just the beginning of the end. Final Thought: 23andMe had a great product, a great mission… 𝗮𝗻𝗱 𝗮 𝗳𝗹𝗮𝘄𝗲𝗱 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝗺𝗼𝗱𝗲𝗹. 🔹 Want to build something that lasts? Focus on trust, sustainable revenue, and profitability—not just hype. ~~~ Follow Gerald Duran for daily startup and VC insights—plus the occasional kick in the nuts. → To land a meeting with us, start here: CanaGlobal (.org) #startups #founders #venturecapital #entrepreneurship