As a young, arrogant fresh grad, I wanted to make an impact. Over the course of four official ventures and many unofficial ones spanning more than a decade, I did make a noticeable dent — but it was never the kind that satisfied me… Perhaps I was unrealistic, overestimating what I could do, but it didn’t live up to my expectations. The idealism and naiveté of inexperience led me down a winding road that shaped me in ways I couldn’t have predicted, but I am grateful for. It wasn’t all flowers and rainbows, in hindsight there were plenty of mistakes that I probably shouldn’t have made.
It’s easy to see a decade of hard work, growth and modest achievements through negative eyes — to feel like things were a failure even though you did the best you could at the time and gain material and immaterial wealth in the process. By many standards, and against many odds, I managed to achieve things that others thought were very unlikely. So if I were to go back in time and give a young entrepreneur like myself some advice, so here’s what I wish someone had told me.
1. Distinguish what users want vs. need
Everyone will tell you to "build something people actually want", which seems obvious but is hard to execute most of the time. Which begs the question where do people stumble in their logic or perception of a situation where they think they are really building something people want, when infact its just how they think things should be. The issues don't come down to core features as those are tangible enough to point at - the issues come down to what the core value offered is.
After making this mistake many times myself, I finally realized something which helped me - core value is subjective and often clashes at the world view or perspective you may have as a new solution provider vs a customer or person who would use your offering. You may think things need to be completely redesigned (and you may be right) but the users just want a simpler way to do xyz instead. The why really depends - switching costs, forcing habit changes, conflicting interests, are just some of the murky implications for the innovation you're proposing... which is the classic chestnut you will endeavor to crack as you build your venture, but we can simplify it as prioritizing what users want, and separating that from what you think users need. In other words, don't get lost in the idealism of how the world should be, at least not early on - focus on the reality and deliver something people already want, that can converge or eventually become what you think they need (but don't expect this to be a linear, clean path). Developing both a strong sense for human nature and reality as well as principled or more logical approaches is the key to winning at entrepreneurship. The innovation is the sauce, its not the bulk of the meal.
2. You’re Pushing Water Uphill
The first thing to internalize is that entrepreneurship is, by definition, trying to cause change against the status quo. To do that successfully takes exceptional effort, talent, persistence and luck (ie. help).
Aside from the cliches of “startups are hard” or “99% of startups fail” or even that “success is about who you know, not what you know”… it’s important to clarify why you think you can succeed despite the odds. You probably don’t a magical way to stop water from rolling down a hill, but you may be able to push that water up a hill because you are passionate or determined.
I didn’t think I needed much help when I was young, that I could push the water myself. Yes I was overconfident, overly optimistic, and smart and hardworking sure but at the time believed that courage was the key differentiator, that taking the leap was the thing that the other smart, hardworking, optimists didn’t have that would set me apart… and I was wrong. I became disillusioned with every failed attempt after failed attempt. But after I was done feeling sorry for myself, I learned that the secret was stamina - to quote Sylvester Stallone from the movie Rocky Balboa:
"It ain't about how hard ya hit. It's about how hard you can get hit and keep moving forward. How much you can take and keep moving forward. That's how winning is done!"
3. The Iterative Lottery
The cliché that it’s a marathon, not a sprint, could not be more true for founders. You need to understand the odds, and you need to understand that those odds have layers.
The key stat here is “99% of startups fail” NOT 99% of founders, and that makes all the difference. Success and failure isn’t measured over lifetimes, its measured on attempts, the more shots you take, the better your chances not only because you got another lottery ticket, but because you have more experience, skills, resources, etc to make a better next short. Your first attempt probably has less than a 1% chance of working, but your 2nd or 10th? Eventually you will figure it out.
Some people say it takes 7 tries, a Harvard study from 2006 implies it takes 5 (for VC-backed founders), but the specific number is unknowable and pointless - the following results are the same.
To succeed you need to try just one more time than you fail, and your best tools as a founder are repetition, iteration, tenacity, grit, and patience. How do you forge those tools? The challenge becomes
a) Finding a mission or business you are willing to go through all these trials and tribulations necessary to succeed (ie. something you actually care enough about)
b) Managing your expectations on when & how you will succeed
(Forget Mark Zuckerberg… statistically, you won’t succeed in your 20s, it’s much later)
There are no magic formulas - you just need to keep buying that lottery ticket. And you need to be able to afford to do it for as long as necessary. So you need to keep pushing and trying different things — adjusting your strategy, challenging your assumptions, earning income another way, and most of all committing to growing as a person, indefinitely.
This growth isn’t just about adding years to your belt, collecting degrees, or stacking certifications. It’s about understanding, exploring, interacting, and collaborating and finding your way, just like in any other career - it is a personal journey of growth.
The good news? There are far more entrepreneurs now and far more appetite for disruption than when I started out ten years ago. There’s also a strong tailwind of technology, tools, and resources that can help founders accelerate their learning — and their fire walk.
4. Entrepreneurship keeps you Young
I often say that I keep doing startups for my mental health, and people think I’m joking. But despite the stress and ups and downs, the amount of fun, learning, new things and great people that you experience along the way are leagues above any other industry or career path I’ve found (and I’ve tried about a dozen different things).
Maybe its the fact that these people aren’t just doing it for a paycheck (you know what I mean), or maybe its because it gives them the most agency and freedom for self-expression… or maybe its the endless pressure to adapt, grow and be better, who knows. But having tried traditional employment and big and small companies in various roles in various cities and at various times - I can say that entrepreneurship is the highest quality signal I’ve found, it’s hard to go back to a 9-5 after you’ve had a taste.
5. You Cannot Succeed Alone
It’s incredibly important to recognize that you cannot succeed in a vacuum. Whether it’s co-founders, teammates, advisors, champions, customers or just a solid network of industry contacts who can open doors and help you figure out what’s going to work — you need people.
They say business is about relationships and I’d say entrepreneurship is the most extreme form of that. In the early days, you probably don’t have much material value or credibility behind the story you’re telling. So it’s essential to leverage the relationships, reputation, and goodwill of people around you who are aligned with your mission or who want to see you succeed.
If you don’t have that network yet, that’s your sign that there is prerequisite work to do. I’m naturally introverted and was definitely not very social growing up, always feeling like an outsider due to being a 1st generation immigrant kid who moved around alot… so this lesson was one of the hardest for me. I was sensitive, took things personally and was scared people wouldn’t want to help me, but now I think people will help you - if you are likeable.
Many founders have a very large vision and skip from A to Z, or try to start from D… but a lot of the first steps come from humility, the willingness to do the work, be open-minded, and practice empathy for those involved.
Putting yourself out there, taking bets, trying to take the smartest bets you can, and constantly thinking about things from different angles — these are tools that accelerate the journey. But acceleration can only go so far.
For your situation ask, would someone want to help you? Solve for that, and they will.
6. Build in Patience
Another toolkit that many entrepreneurs need to be honest about is patience. Going from A to Z is impossible in one leap. To iterate on your lottery ticket until you finally break through takes enormous patience. You may think you have the best strategy since sliced bread, but chances are it needs refining. And the chances are even higher that the industry or people you want to help or ask for help won’t move as fast as you want (because, well, they have a life, unlike you).
So it’s vital to have a sustainable lifestyle, to find ways to manage the stress that will break down your will, your health, and your personal life. You need to maintain the effectiveness, focus, and productivity required to succeed — and those demands only increase the busier and more successful you get.
You also need to be honest with yourself and do the work necessary to succeed. Maybe your business plan is wrong or will take twice as long to achieve… prepare for that. The world will politely punch you in the face until you do. As Mike Tyson said (I’m not even big boxing guy...):
Everybody has a plan until they get punched in the mouth.
7. Navigating Industries
It’s important to understand how the market you are going to operate will work: that there are special interest groups, entrenched biases, and significant resistance to new players with disruptive ideas - and that each industry or market has its own unique culture. Some love tech, many don’t. Some are ripe for an update, many aren’t, but ultimately none are easy. As the strategic stability of Nash Equilibrium goes - each industry or market tends towards a state where it is equally competitive, if there ever was easy money to be made it is quickly wrung out of the system and the situation always approaches its own unique series of challenges and high competition.
The typical entrepreneurial life cycle is ignorant optimism followed by informed pessimism, and then jumping onto the next thing… which, I’ve been guilty of thinking the grass is in another business or market, but naturally most grass isn’t that green and how well you fair in one grass over another depends on you.
You may talent or contacts or just fit in better in one industry over another, or the timing may be better over here over another, but ultimately you need to be able to spark change in that audience. If they won’t listen to you or trust you… then you need to really reconsider why, and if it isn’t worth fixing that for you, then you can justify moving on. Although you want to make things better, you must accept that:
To be an entrepreneur is to be counterculture.
To be an entrepreneur is to be controversial.
To be an entrepreneur is to be disruptive.
Unless you can recognize you are an edge case and navigate the mainstream with savvy, it will be very hard to succeed. You can’t walk into a party, start singing your own tune, and expect everybody to drop what they’re doing and listen — even if your tune is objectively better than what’s already playing. People aren’t fully logical. Emotionality plays a big role in most markets. Incumbents have moats and ways of maintaining their positions that, while not future-proof, are usually quite strong. If you don’t know anyone at the party or they don’t like you… they will make your journey alot harder than it already is. Make them like you, if they don’t already.
Learn the difference in characteristics and behavior in early adopters, find a small circle of fans — people who believe in technology and want to see the change you’re bringing to a specific industry — if you can’t find this, reconsider if there is “Founder-market-fit”.
8. Watch Out for the Vultures
Meanwhile, it’s important to be wary of the trolls, opportunists, and vultures sitting along the startup ecosystem. Many people are well-intentioned and helpful, but many are not, and the loudest or most active ones often are over-compensating for something.
Institutional investors or VCs are not your friends. They are in it to make the biggest, fastest profit they can, and are playing a game that is stacked against founders. Again while some are good, the nature of the game is to treat founders and their startups as just a number. They have the resources, the network, and the experience to take advantage of most inexperienced people, and over the past few decades as the innovation industry has matured, they have setup startup factories and founder recruitment like war generals, I won’t name names or judge people who participate but just be aware that you are one of many, many founders they talk to. They structure deals to prioritize investors outcomes and control - minimizing founding teams both in terms of autonomy and payout. This is controversial and few will say it — because saying it limits your chances of getting their money — but it’s important to point out if you have integrity or want control over your business long-term, and are not just out to pump and dump for a quick buck.
The next type to watch out for is those who appear to be your friends: an advisor, a consultant, maybe a coach. At best, they try to help but don’t offer enough value to justify what they’re asking for (always err on equity not cash payment). At worst, they’re trying to take advantage of your ambition or ignorance and charging you some big upfront fee or unjustified equity/role. You are not in Kansas anymore, Dorothy, there are many predators one encounters down the yellow brick road to the land of Oz.
Take every offer or opportunity conservatively, look for those who offer value upfront or have skin in the game with you. Hitching your wheels to the wrong person or direction carries massive opportunity cost - I’ll admit it’s wasted years of my life and was seeded on some desperate desire for someone to come “save me”. While it’s impossible to know with certainty who’s right for you, if you take your time, get to know people, and don’t rush things, you have a much better chance of filtering out bad partners.
Angel investors are the best, if you can find them. They are a rare and dying breed that actually believes in the founder, mission, company and has a more reasonable approach to investing which usually makes more sense. But many people masquerade as Angels to get your guard done, but they are in fact not. If their offerings do not tangibly show an understanding that you are cash-strapped and want to stay in control... they may not be as founder-friendly as they claim.
9. Be Proactive, Not Reactive
The easiest way to protect yourself is to be proactive. In the same way that your long-term vision is one of your biggest assets, you need to apply that foresight to the short and mid-term — with people and with everything you do.
Look for advisors, teammates, investors or any help before you really need it. This gives you the time and discretion to weigh your options. You’ll be less likely to jump into business with someone because you need their money or know-how right now and idolize them to convince yourself this is a good opportunity, when it really isn’t.
It’s equally important to not be complacent — don’t only reach out to one person, or whoever has come to you. That’s a narrow approach that doesn’t even maximize your luck surface area. Take a wide survey of the field. Talk to multiple people. Seek out those you think are the best for what you need, or are referred to you by people you trust, not just the ones who think they’re the best for you.
10. The Art of Picking People
Just like your vision and judgement can be honed to help plan for situations, it can also help you develop your intuition for people. Co-founders and teammates are even more critical because of the commitment and long-term impact they’ll have on your venture. I’ve been burned by hiring and collaboration decisions more times than my fair share.
It’s important to hold your judgment of people — understanding their character, how they fit with you, and whether you have complementary skills. It’s not that most people aren’t good; it’s about whether you have aligned incentives and can agree on what is a fair collaboration. As Warren Buffet says:
“You can’t make a good deal with a bad person.”
(let’s soften the definition of “bad person” as someone with different values than you).
Building relationships, managing them, and picking the right ones is some of the trickiest work you can do as a founder. It’s typically not a skill you develop any other way. If you’re a technical person or a marketing employee, you don’t usually have to hire people or develop a sense for how well you can work with someone under pressure. And picking good friends doesn’t translate to picking good work partners — even your best friends are different when it comes to work.
This is another iterative lottery you need to play to develop a sense for people. That said, stay open-minded. Hear people out. Give them a shot — maybe not in a risky, committed way, but through trials or just spending time together and learning about their past work.
11. People Buy From People They Like
When it comes to interacting with customers and the market, this skill matters too. People buy from people they like, and if your intentions aren’t clearly good, it becomes hard for people to trust you — especially in today’s age of brand authority and hyper-fragmentation.
Taking a people-first approach to technology and entrepreneurship can help de-risk and accelerate probably 80% of what you need to do.
Of course, knowing what to look for, who to talk to, and how to approach things isn’t purely a guessing game. Having a strong sense of what you want to build, why you want to build it, and the strategy behind it is paramount.
If you’re someone with strong domain experience or a unique market insight, that can seem obvious to you — but unpacking it and developing the right strategy to move from A to B to C is not trivial. People often take it for granted or don’t realize they’re relying on intuition rather than explicit logic. Slow down your thinking. Dissect the reasoning behind what you’re trying to do. This helps you refine your approach, filter out misconceptions, and guide the kind of networking, outreach, and communication you need as you build. Again learn to spot early adopters and study what they like and how you overlap - a mass movement has to start somewhere, pick wisely.
12. Create 10x Value, Expect 10% Wins
It’s important to focus on creating deeper value. If you can offer something twice as valuable as an existing solution, that often isn’t enough. Many say you need 10x value to overcome the cost of change — to convince people to give up comfort, security, and habits they have, and go through the significant effort of switching systems or convincing their team to take a chance on you.
You need to be the highest-value and most likable person in the room, with very strong conviction about what you’re trying to do. And even then, expect a lot of rejection. The vast majority — say 90% — of any demographic, whether customers, potential advisors, partners, or investors, still won’t match with what you want. They won’t be the early adopters. They may have competing interests.
Have a thick skin. Don’t take rejection personally. Be proactive. Don’t let it put you off or make you bitter. Keep trying and pushing until you find the right people. When you find the 10% that are early adopters who “get it” and build some momentum, they will help you gradually expand into the rest of the market in more ways than you can imagine.
13. Move the Herd
Think about it with a herd mentality. You don’t move a herd all at once — you convince a select few to start moving, which influences others around them, which cascades through the group until you’ve created a mass migration. This society-level observation of technology adoption life cycle and Geoffrey Moore’s famous distinction of the chasm between “early-adopters” and the “normies” (ok, that’s my wording) is truly worth fully digesting and integrating into the way you think about markets.
This granular, patient approach is key to making the market work. It’s something we live and breathe at siift. We’re able to move quickly given AI — both as a tool for our own development and as a market force creating pressure — but while we’d always like to move faster, there are realities we need to face.
The concept of being “too late” to a market is usually wrong. It’s usually hyper-panic instilled by investors, the media, or incumbents… but taking your time and building something of quality — the right way, with solid foundations and the right people — is a proven approach to building a durable, meaningful company that creates the kind of change in the world, and in your own life, that you’re looking for. Many times the second players or those with superior technology wave leverage are the long-term winners.
14. The Real Product
Fifteen years in, I still don’t have it all figured out — and I’m skeptical of anyone who claims they do. Especially as the ground moves beneath our feet faster than ever, with the rate of tech progress and changing world affairs.
But I do know that the version of me who started this journey wouldn’t recognize the person writing this, and that’s the point. The ventures themselves are just vehicles. The real product of entrepreneurship is who you become through the process — more patient, more discerning, more humble, and paradoxically, more willing to bet on yourself than ever. If you’re early in this journey and everything feels impossibly hard, that’s not necessarily a sign you’re doing something wrong, you’re just learning the game (and probably faster than most). As you grow things will feel easier… not because it is, but because you got better.
Tired yet?
If you want to accelerate your entrepreneurial journey, siift’s Founder Intelligence Platform can help you do more systematic ideation, validation, and go to market activities, while reducing the biases, blindspots, and distractions that plague founders and new businesses. It can give you applied, real-time guidance that is context aware to your specific situation… and not just another business advice blog post :)