Lessons Learned From Failed Market Entry Strategies

We grew by 57,000% in 3 years. Then we made a colossal mistake. Quest Nutrition exploded out of the gate. The company was born on the back of a mindset, and we wanted our customers to know that too. So we launched Quest Apparel, a lifestyle brand around the relentless pursuit of maximizing your human potential. Why haven’t you heard of it? Because we shut it down. It failed. Hard. What Quest meant to me as a founder wasn’t what it meant to the consumer. And only the consumer matters. It suddenly became clear to me that Quest launching a clothing company was like Quaker Oats launching a clothing company. You may love Quaker Oats, but do you want to wear an upscale $120 henley made by them? No. Here’s how you can be wise and learn from my mistakes… 1st: Establish Your Brand’s Core Identity. We tried to establish an aggressive, edgy vibe without considering the brand identity we’d already created in the mind of our consumer. Quest Nutrition is about healthy, delicious food. It was fun, playful, and inviting. Launching a sister brand that was aggressive and cool was a total mismatch. 2nd: Understand Your Audience. The influencers that promoted our brand were in shape, but the people actually buying our products were trying to get in shape. So clothing tailored for people with the perfect physique didn’t work. If we had launched an athleisure brand aimed at flattering people trying to improve their physique, we might have had a shot. 3rd: Create Straight Lines. Whenever you’re doing something new, ask, what’s the straight line between the marketing and the product? If you can’t see the straight line between the high performing piece of content and the product you plan to sell, odds are you should stop immediately as there’s no alignment with your current audience. That doesn’t mean you’re dead in the water, but it does mean that: 4th: If You Want To Change Lanes, Pave The New Lane First. As I would learn once again when I launched a comic book, brand goodwill doesn’t automatically transfer to new products. Just because people like my interviews, doesn’t mean they even read comic books, let alone like MY comic books. If you want to go into a new area, develop the new straight line. Start creating content that will build the audience that will buy the thing. Don’t go to all of the trouble of building the thing without knowing if you can create content that will attract the right audience. Content is MUCH easier to experiment with than products. If you get strong results with the content, then build the product. If you stay true to your brand’s core, understand your audience, create straight lines, and always build the audience before you create the product, you’ll be able to evolve your business. But if you don’t do that, you’re going to burn a lot of money. Take it from someone who’s burned millions so you don’t have to.

5 Mistakes I Made Launching in the U.S. Market (So You Don’t Have To!) 🇺🇸 Expanding Stand4 Socks from the UK to the U.S. was always going to be a challenge—but I underestimated just how different the markets really are. Now, 18 months in, we’ve made some big wins, but we’ve also learned some tough lessons along the way. Here are 5 mistakes I made when launching in the U.S.—and what I’d do differently: 1️⃣ Thinking What Worked in the UK Would Work in the U.S.  I assumed our marketing playbook from the UK would translate directly to the U.S.—it didn’t. Customer behaviors, expectations, and even the way people shop are different. From designs to messaging, things needed tweaking. 💡 Lesson: Treat the U.S. as a fresh start, not just an extension of your existing market. 2️⃣ Underestimating the Cost of Logistics & Operations  Shipping, warehousing, and fulfillment costs are way higher in the U.S. than in the UK. The country is massive, which means delivery expectations (hello, Amazon Prime!) are tough to meet profitably. 💡 Lesson: Plan logistics early and find reliable partners who can scale with you. 3️⃣ Don't think to small, don't be "too British" Amount of times I have been told 'your being too humble, you're too British'. I am not a one to fake it till you make it, but American culture reacts better to ambition and thinking big - the American dream. Balance your narrative. 💡 Lesson: Tailor your message to you audience, while sticking to your values. You can think big without being misleading, get people excited by the journey. 4️⃣ Embrace the network effect sooner - get out there. The USA loves an entrepreneur story, no matter your stage. In the UK I always feel people mostly care 'once you have made it' - whatever that means. However in the US people actively want to help and make introductions, no matter their background. Build your team fan base and engage early. 💡 Lesson: The answers already no, so whats the harm in asking the question. The incredible people I have met, connections introduced too are beyond my wildest dreams. Connect the dots. 5️⃣ Not Having U.S.-Based Team Members Soon Enough  Time zones, cultural nuances, and on-the-ground connections matter more than I thought. Having a local presence (especially for sales and partnerships) is a game-changer. Although costs are way higher, especially in New York so be smart a build partnerships. 💡 Lesson: Even if you’re bootstrapping, find U.S.-based reps, freelancers, or sales partnerships as early as possible. 🚀 Final Thought: Expanding internationally isn’t just about launching in a new country—it’s about adapting, learning, and being willing to pivot. The U.S. has massive potential, but you have to play by its rules and respect it. Ps take your dog (socks!) to more meetings. #Startups #LessonsLearned #USMarket #ScalingBusiness #Stand4Socks

Let me share a story that will hopefully change your perspective on looking too narrowly at information about a new location. The store looked perfect on paper: → High foot traffic area → Growing neighborhood → Competitive lease rates and attractive allowances → Strong demographic match But within six months, the retailer was struggling to keep the lights on. The location ultimately closed, but here is what the retailer told me about their changed perspectives (learnings): ✓ Data doesn't tell the whole story. Without 𝗯𝗼𝗼𝘁𝘀 𝗼𝗻 𝘁𝗵𝗲 𝗴𝗿𝗼𝘂𝗻𝗱 𝗮𝗻𝗱 𝗹𝗼𝗰𝗮𝗹 𝗺𝗮𝗿𝗸𝗲𝘁 𝗸𝗻𝗼𝘄𝗹𝗲𝗱𝗴𝗲 (lmk), they missed many neighborhood and property nuances ✓ Consumer patterns aren't just about location. The consumer has deeply established shopping routines that hadn't been considered and were going to have to shift for the store to have been successful → Timing matters. A major road construction project changed traffic patterns right after their opening (local market knowledge would have identified this coming impact) What would they do if they had to do it over again? → Spend time more closely observing local shopping patterns (boots on the ground) → Adjusted operating hours to match community rhythms (understand personas) → Modify product mix based on actual demand with an understanding that the consumer is truly unpredictable (supply chain management) → Build relationships with neighborhood leaders, business and property owners (local market knowledge) Remember: ⚑ Location decisions are a blend of art (lmk) and science (data) ⚑ A 𝘯𝘰 can be just as important as a 𝘺𝘦𝘴 ⚑ 𝗙𝗮𝗶𝗹𝘂𝗿𝗲 𝗰𝗮𝗻 𝗯𝗲 𝘆𝗼𝘂𝗿 𝗴𝗿𝗲𝗮𝘁𝗲𝘀𝘁 𝘁𝗲𝗮𝗰𝗵𝗲𝗿 𝗶𝗻 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀

We brought a proven play park franchise from Spain to Switzerland. Everything looked perfect… until it flopped. The model was solid. The brand was strong. And kids? They love to play anywhere. So why wasn’t it working? Because we focused on the model and missed the context. The culture. The routines. The family schedules. They didn’t match. In Spain, late-night play worked because families lived on a later schedule. Dinners ran late, and kids played into the evening. Switzerland? Early schedules, structured routines, and a culture of predictability. We noticed the differences from the start. But we assumed they’d adjust to us. The model was already proven, right? Wrong! People don’t change their habits to fit a business. Businesses need to adapt to the people. At this point we had 2 choices: ❌ Force what worked elsewhere. ✅ Adapt to what works here. We adjusted our hours to fit Swiss routines. The results were immediate. Lesson learned: ❌ Success isn’t about forcing a formula. ✅ It’s about recognizing signals and adapting fast. Because things work… until they don’t. When a proven model stops working... Those who refuse to adapt will be replaced by those who do. You can cling to what worked yesterday. Or adjust to what works today And keep an eye on tomorrow. → Adapt. → Evolve. → Move forward. Or make way for the ones who will. ResetMindset #MindsetMatters #Productivity #ClarityOverChaos

One of my companies raised $3.5M. Earlier this year, we shut down. Here’s what I learned from failing: In 2021, I started work on 3 businesses. One was Kahani. It was like Instagram stories for ecommerce: log on, see circles in the header and tap through videos. The prototype showed clear demand. While I’m bootstrapped at heart, I decided to raise money for Kahani. Investors were in, but only if I was CEO. I didn’t want to be a CEO at this point in my life. Somewhat reluctantly, I agreed. My plan was to transition to another CEO later on. After a relaunch, we had $10k+ MRR and a solid new design, but we also had expenses of $60k+ / mo. We were burning $50k every month! I was sick to my stomach. I’m a disciplined bootstrapper. I had NEVER seen a P&L that lost money! This was a MASSIVE problem. I’d walk into investor meetings ashamed. I tried to find a way around it, but you can’t force product-market fit. I had to swallow my pride and tell my investors that we couldn’t keep running this business. I arranged to reimburse the investors. I emerged from this failed project with 4 main takeaways: 1/ Trust Your Intuition: From nearly the moment I agreed to be CEO and we raised money, it didn’t feel right. I told myself the feeling would pass. But it didn't. I neglected my own gut feeling. I could have saved myself and others a lot of time and energy by honoring my gut. 2/ Sales Come First: Hunting for product-market fit in software is HARD. At my other companies, I didn’t search for PMF. I proved my ideas by generating sales. GrowthAssistant, Aux and Bootstrapped Giants cannot keep up with demand. Kahani never really HAD demand. 3/ Communicate Candidly, Early and Often: When we decided to move on, the investors were impressed by my honesty and quick resolution. So were employees and others. I don't think I burned one bridge. Instead, I strengthened many. This is one silver lining I can be proud of. 4/ Know the Difference Between COOL and GOOD Ideas: A good biz idea solves a REAL problem. Kahani was a COOL idea. ...but not a GOOD one. GrowthAssistant (offshore marketing talent) solved a REAL problem, making it a good idea. This distinction will MAKE or BREAK your biz. As an entrepreneur, you WILL fail. It’s up to you what you make of that failure. Never make the same mistake twice.