Understanding the Challenges of Startup Life

I got asked what the most challenging part of the journey has been at Superfiliate The answer was so uncomfortable 🙃 but I think it will resonate with other operators and founders The darkest part of the journey was the first 3-6 months of finding product market fit in the midst of having employees, investors and early customers. In some ways, you're living multiple lives where you have varying degrees of confidence and conviction about what you're building. Even if you’re not a founder, you feel the same varying conviction around all new initiatives that you’re taking on. Externally… you have to be ruthlessly confident in what your product/idea is (and really what your product WILL be in the future, but is not today) You have a story that tells that narrative. It’s very theoretical, built on intuition and aspirational at best. External stakeholders include potential investors, customers, members of your team or even family/friends. Internally… you're running this calculus of where you need to play devil's advocate to push the product or idea to where it needs to be AND how you communicate that effectively to those external stakeholders. You’re trying to convince yourself enough to be able to speak with confidence while also being your biggest skeptic to see the holes in your product vision. The risks are huge here. Let’s just take your personal mental health. Your brain is in a constant state of flux, oscillating between safety and threat. The parasympathetic and sympathetic nervous systems are fighting for center stage. You feel safe when external stakeholders or the market validate your idea. Then the terror sets in when you realize that one point of validation is but a drop in the bucket towards getting your product or idea to where it needs to be and how much work is in between now and then. The other risks include your customers, investors or teams confidence in your ability to drive innovative & well thought through business decisions, while knowing that there’s a constant tradeoff between intuitive vs data-driven decisions. It’s all so uncomfortable 🙃 You feel it every day. You can talk and confide in others about it… but you’re still the one that needs to build your way out of it. This can last months or years, at Superfiliate this lasted 3-6 months. We were very lucky that our customers, investors and team were extremely entrepreneurial minded and comfortable in this uncomfortable space. It was still a challenge. The ugly truth of product market fit is that it sounds like a static achievement but it’s more of a dynamic and ever moving target. Once you reach one level of PMF there’s a new set of challenges, tangental market opportunities and threats around the corner and a whole other round of this same cycle. Ideally, you find the capacity to love the flux. To recognize that the flux creates the pressure of being your biggest skeptic while also powering the confidence to speak your product or idea into existence.

This is the death spot for startups: Not quite failing, not quite succeeding. Stewart Butterfield (Slack founder) said it's the "hardest moment in a startup's life.” You're telling a story that people want to believe in, but reality keeps punching you in the face. I've been there, too. You're working insane hours, for months on end — trying everything to move the needle. But nothing quite sticks. Or parts stick, but not enough of the whole. You're not failing hard enough to call it quits, but you're not succeeding enough to feel confident. It's a special kind of hell. How you handle a middling time like this can make or break your startup. You have three options: 1. Keep pushing forward 2. Pivot to a new strategy 3. Quit and cut your losses None of them are easy. More often than not, your gut will guide you to the right decision. Maybe that means doubling down. Maybe it means pivoting to a new strategy. Maybe it means living to fight another day. Whatever you choose, trust yourself. Start by asking: • Do I still believe in the mission? • What are our strengths and weaknesses? • What can we do differently? • Are we serving the customers we initially thought? • What do our customers really want? • Is our product genuinely valuable? • Are we sure we’re in the right market? Take the time to really sit with these questions. Talk with your team. Ask your advisors. Consult your mentors. But at the end of the day, the decision has to come from YOU. Because here's the hard truth: There is no right answer. There's only the answer that feels right for you and your startup. But you need to be opinionated and make a decision no matter what… Because a bad decision has a chance of killing your startup. But indecision will kill it, guaranteed.

As an innovation educator, I've seen countless entrepreneurs struggle with changing environments as they grow and that's why I invested over a decade in trying to understand why. In our upcoming book "Nail it, Scale it, Sail it - The Innovator's Odyssey" we explore the unique challenges and strategies for each stage of the innovation journey. 1. Nail It: Surviving the Jungle The Nail It stage is like entering a dense, unfamiliar jungle. It's hot, stuffy, and filled with strange sounds and smells. The environment is unpredictable and resource-constrained, requiring extreme agility from the small team. In this stage, innovators must embrace a culture of frugality and customer intimacy. They need to know all their customers, learn what they need, and react fast to errors. Speed typically overrides quality, as a minimum viable product tested early in the marketplace will do more good than waiting for perfection. 2. Scale It: Conquering the Mountain Scaling is like embarking on a daring expedition up a long, steep mountain. The environment becomes clearer, with visible paths and a sense of direction. However, it's a paradoxical adventure that demands both expansion and refinement. As Bob Sutton of Stanford School of Engineering points out, "Scaling is a problem of less. There are lots of things that used to work that don't work anymore, so you have to get rid of them." In this stage, innovators must shift from "what" to "how," balancing growth with structure. They need to streamline processes while expanding, cultivating resilience and discipline. Like Dan Gilbert said, "Ideas are rewarded. Execution is worshiped." This stage is where your ability to execute efficiently at scale becomes paramount, all while maintaining the innovative spirit that got you here. 3. Sail It: Navigating the Open Seas The Sail It stage is like navigating open waters. Growth has decelerated, and the focus shifts to sustainability and continuous improvement. The environment is more stable but still competitive, requiring vigilance and swift adaptation to market dynamics. In this stage, innovators must leverage data for decision-making and manage complex resources effectively. They should embrace a culture of continuous improvement, optimizing processes and refining operations. As the company's visibility expands, maintaining a strong brand reputation becomes crucial. It's about staying innovative while optimizing operations, ensuring the company can weather any storm while still charting new territories. Remember, what works in one stage may hinder you in the next. The key is adapting your mindset and strategies as you progress through these distinct environments. Curious about the 'why' behind these stages? Stay tuned for my next post, where we'll explore the fundamental reasons driving this innovation journey.

Starting your own business is often glamorized as the ultimate career move. Being your own boss, setting your own rules, and the potential for unlimited income. But what about the side of entrepreneurship that doesn't always make it into the spotlight? The ugly side. Well that's what I'm going to reveal today (and I'll make it shortish and sweet). Here's the top 4 things I wish I understood before setting out to start my own business: 1. Failure is part of the process. When you start out, hitting that 10k MRR may seem to perpetually stay on the horizon. Some of your business ideas may fail before they begin to pay off. The key is resilience. It's about the ability to dust yourself off and continue fearlessly, learning from each setback. 2. The entrepreneurial clock doesn't follow office hours. The romanticized idea of a 9 to 5 schedule rarely syncs with the reality of entrepreneurship. There will be late nights and early mornings, trade-offs, and sacrifices. It is best to understand this and commit to doing whatever it takes before starting, than learning the hard way. Trust me. 3. The learning curve isn't a gentle slope. As an entrepreneur, your role is ever-evolving. From understanding the nuances of sales, delving into marketing strategies, getting hands-on with product development to navigating the complexities of taxes, it's a constant learning process. I keep a notion document and make sure to record everything I learn with links to resources that I found valuable. This has made the world of difference for me when it comes to organizing all of the new information I have to understand and master. 4. Top-tier solitude. As a leader, decision-making can be a lonely business. It's often you who has to make the hard calls and bear the responsibility for the outcomes. Forming a network of like-minded entrepreneurs can be the grounding force in this whirlwind journey. I would also recommend finding a co-founder that compliments your skillset as you go down this path. I can't describe how many times I have ran into issues I had no idea how to overcome that my co-founder stepped in and solved with ease. Life and business are much more enjoyable when you have people you trust and can count on. Yes it is daunting to start your own business. Yes it is hard. Yes you're going to fail over and over until you succeed. But, what's even harder than starting and failing, is never trying and living your entire life wondering "what if?".

The TOUGHEST phase of growing a business? Sure, scaling is hard. But the real beast is the start-up stage. Why? Let's break it down: 1. You're selling a dream. No track record. No proof. Just your vision. 2. Cash is king (and you're broke). Limited resources. Endless expenses. Fun times. 3. Customers? What customers? Building a client base from scratch is brutal. 4. Work-life balance? It's a myth. Say goodbye to sleep. And weekends. 5. You don't know what you don't know. First-time founder? Prepare for some costly lessons. So, how do you survive this gauntlet? → Plan carefully. → Embrace low-cost, high-impact resources (think Virtual Assistants and AI) → Know the market inside out. → Watch that cash flow like a hawk. → And most importantly? Don't. Give. Up. What was your toughest start-up challenge and how did you overcome it? Let me know. P.S: Follow me for more content like this.

Building a startup is thrilling—I love it so much, I've done it 9x. But let's be real: Success is never easy, and it certainly isn't free. 𝗪𝗲 𝗽𝗮𝘆 𝗳𝗼𝗿 𝗶𝘁 𝗶𝗻 𝗺𝗼𝗿𝗲 𝘄𝗮𝘆𝘀 𝘁𝗵𝗮𝗻 𝗼𝗻𝗲. 𝗧𝗵𝗲 𝗜𝘀𝗼𝗹𝗮𝘁𝗶𝗼𝗻 𝗧𝗮𝘅: Being a founder is lonely. Other people might not understand - that's why we built startups.com because we want to be a part of a community that supports each other and just 𝘨𝘦𝘵𝘴 𝘪𝘵. 𝗧𝗵𝗲 𝗪𝗮𝗶𝘁𝗶𝗻𝗴 𝗚𝗮𝗺𝗲: Early wins can fade as fast as they came. Fast-paced is not really growth and gains but just a guise for a 𝘁𝗼𝗻 𝗼𝗳 𝘄𝗼𝗿𝗸. The real journey is prolonged periods of uncertainty and anticipation. You have to be in it for the long haul. 𝗧𝗵𝗲 𝗙𝗶𝗻𝗮𝗻𝗰𝗶𝗮𝗹 𝗚𝗮𝗺𝗯𝗹𝗲: Building a startup isn’t a get-rich-quick scheme. It's a ton of cash burn before we even see the light at the end of the tunnel. 𝗧𝗵𝗲 𝗥𝗲𝗹𝗮𝘁𝗶𝗼𝗻𝘀𝗵𝗶𝗽 𝗦𝘁𝗿𝗮𝗶𝗻: Balancing startup life while maintaining our relationships can feel like an uphill battle - but as much as we pour ourselves into our work, we can't neglect the relationships that anchor us. High stress, anxiety, burnout, depression, and even panic attacks - 𝘵𝘩𝘦 𝘨𝘳𝘪𝘯𝘥 𝘤𝘢𝘯 𝘵𝘢𝘬𝘦 𝘪𝘵𝘴 𝘵𝘰𝘭𝘭 𝘰𝘯 𝘶𝘴. Startup Snapshot sheds light on the unspoken journey of startup founders 👇 At the heart of it all, 𝘄𝗲'𝗿𝗲 𝗼𝗻𝗹𝘆 𝗵𝘂𝗺𝗮𝗻. We can't do everything, especially not on our own. 💬 It's time for us to have an honest conversation about the true costs of entrepreneurship — 𝘵𝘩𝘢𝘵'𝘴 𝘩𝘰𝘸 𝘸𝘦 𝘤𝘢𝘯 𝘵𝘳𝘶𝘭𝘺 𝘴𝘶𝘱𝘱𝘰𝘳𝘵 𝘰𝘯𝘦 𝘢𝘯𝘰𝘵𝘩𝘦𝘳. Startups.com: 𝗕𝘂𝗶𝗹𝗱𝗶𝗻𝗴 𝗦𝘂𝗰𝗰𝗲𝘀𝘀, 𝗧𝗼𝗴𝗲𝘁𝗵𝗲𝗿 🚀 #MentalHealth #Entrepreneurship #Startups #Success