17 Lessons Every Entrepreneur Learns Along The Way To Success
I failed at two companies, but the third one is my charm.
I’ve been trying to start a successful company full time for the last four years and am on my third try.
From the bottom of my heart — full time growth entrepreneurship, as in, traditional investor backed product / industry disruptive innovation is the greatest, fastest, most meaningful teacher of all time.
Other people’s money on the line.
Your reputation on the line.
People counting on you.
If you want the wisdom and growth of forty years in four, full time growth entrepreneurship is the time slipstream to make that happen.
My Biggest Mistake
My biggest mistake was underestimating the shift in psychology required that results from transitioning from a paycheck earner, receiving your sustenance on a predictable day of the month, to 100% self-reliance — to producing on my own. Add tight constraints and competitors to the equation and it changed my world.
· The scraping for inches to win.
· The ups and downs.
· The weight on my shoulders because of the pressure to perform.
· The responsibility of other’s survival.
· My family and friends watching you all the time.
· My product being my baby.
Will women want to date me anymore? I earned an average of $250k a year for four years at my last start up and became accustomed to a certain lifestyle which had to be cut.
It’s been a man maker these last four years but I’m beginning to see the light.
Ultimately, I realized, the key to succeeding in entrepreneurship boils down to lasting, and being resilient enough to find joy in the process to finally thrive with yourself and through that, your business.
- Joy in the ups and downs.
- Joy in the game.
That’s when you’ve won the war before the first battle and can execute.
That’s when you’re in a daily state of calm flow that takes everything in stride and has a plan for it all.
That’s when you’re always cutting through the fat of everything with extreme presence.
This is why my mantra that drives me each day is “presence must be like breathing.” — Josh Waitzkin
Here are 17 personal lessons and stories of what I learned first hand, to become that resilient person who derives joy from the day to day ups and downs of entrepreneurship.
1. The Idea Is Personal and Needs to Be Meaningful To You, Or You Need a Strong Why To Win
“He who has a why to live can bear almost any how.” — Friedrich Neitzche
Entrepreneurship is like pushing a heavy rock up a hill so at some point, you always ask yourself why you’re doing what you’re doing. There are many ways to make money, so why do I choose this particular way?
My first business was a people platform that had the wrong ‘why’. It was ‘sexy’, but my motives for starting it weren’t correct. Given I came from a media and conference background, I figured I’d do events ‘my way’. So I rented a 6,000 ft. live/work space in Manhattan, and produced some of the best live salon gatherings and events the world had seen.
It was my first go and I went in excited. Drunk off the “bug” of entrepreneurship. I was intimidated moving to New York so I wanted to make a splash — but I wasn’t ready.
I wasn’t as good a public speaker as I needed to be.
I didn’t have the proper framework to think through the business.
I didn’t understand markets, human nature and competition.
I didn’t understand why people buy.
My ‘why’ was “he’s an entrepreneur” and “he’s doing something cool”.
I learned the hard way and made mistakes.
However, the beauty and curse of it all is that it took this deeply painful and expensive hard lesson to get these lessons burned in me.
2. Assume It’s a 10–15 Year Commitment Because To Succeed It Most Likely Is
Sure, you vest stock every year and can put in four or even less, but if that’s your attitude going in, you’re likely being too short sighted and aren’t excited about your idea and vision. Plan for 10–15 years and you dig deep and ask questions like:
· What do I stand for?
· What do I want to be remembered for?
· How do I want to earn my money and be remembered by?
· What are my alternatives?
· Will this bring me fulfillment if we achieved our goal?
· What is my goal with the company?
· Do I even want to be an entrepreneur? What’s driving me?
All these questions become inevitable, and needed to be asked before I started.
I made the mistake of diving into the wrong idea for the wrong reasons. I’ve pivoted twice to not so much find the idea that’s ‘right’, but I have the principals within me to assign meaning to it and my ‘why’ for winning and succeeding at something hard is correct, so I now feel confident we’ll win even though we’re facing our own day to day obstacles and adversity.
3. Embracing Pain For Personal Growth And Finding Joy In The Journey Is The Mindset You Need
“The winners have already won, and feel as though they’re in possession of the success they want with their company.” — me
In my first company, I was letting the stress get to me running around to get as much done as I could — and I never rested. My second try was a little better having observed the mistakes of my first one, though I was still in a frantic state of wanting with my back against the wall. This is the misnomer of successful entrepreneurs, that they’re always intense and hard charging.
This isn’t true. The best are calm, and exude a steady intensity ready for the marathon.
Now I do everything I can to work in a steady state of presence. I know the game is a long one, and I’m content winning with a salary, owning a decent enough of the company to create some wealth in the future, and having a positive and productive lifestyle and culture among my colleagues and personal relationships.
4. Your Business Can Only Be as Big, To The Extent You Become Resilient
“Your business can only be as big as you are.” — Tony Robbins
This means an emphasis of personal growth is key. This is why you see entrepreneurs, more than anyone else, doing everything they can to win an inch. Whether it’s intermittent fasting for a mental edge or sleeping at 8:30pm four nights a week like I do to begin their days at 4:30 in the morning to get in their best state. It seems the more physical the better because focus and decision making are so critical. I haven’t had a drink of alcohol in four years because of my commitment to succeeding at entrepreneurship.
5. Learn To Love Winning And Competition
“Every minute you’re not working, someone out there is working hard to beat you.” Marc Cuban
Though I hate admitting this you need to want to win more than you want to breathe.
Better yet, the meaning you assign to every moment you have needs to be a winning moment — the right state, intentional and purposeful.
The good news is is this can become manufactured, in a way that is still positive and aligned with integrity.
This is why many entrepreneurs sometimes take it too far and do things to win that aren’t ethical. The landscape is so competitive that embracing winning against the other guy becomes your “why”. You’ll do anything to win. Taking short term inches to long term planning, all to out-do the competition. An attitude obsessed with winning becomes almost required because of competition in the markets.
How you choose to let it manifest is a reflection of you the entrepreneur.
6. Learn To Always Look For Unfair Advantages
“The best entrepreneurs know this: every great business is built around a secret that’s hidden from the outside. A great company is a conspiracy to change the world; when you share your secret, the recipient becomes a fellow conspirator.” –Peter Thiel
You learn how ruthlessly efficient markets actually are and any advantage to exploit must be jumped on. Competitors win with unfair advantages.
- A key relationship.
- IP that no one else has.
- Insights and a vision you see for a better world that others don’t (this is an underestimated one) care enough about.
I didn’t believe the tails of corporate espionage and all the rest of it from the movies, but now I do as I’ve seen situations first hand of people taking extreme measures to win an inch. Fortunately, you don’t have to go this far and the good old virtues of hard and honest work tend to outlast the competition over time.
However timing the market and product market fit are a must.
7. Be Aggressive
“Only those willing to go too far will discover how far they can go.” T.S Elliott
This should be both in character and appetite for risk. The best employee I’d ever seen, who after six years rose through the ranks as fast as I’ve ever seen anyone rise at a company, also happened to be the most aggressive person I’d ever come across.
When in doubt, he’d pick up the phone and call.
When in doubt, he’d call the CEO and ask for the order.
When in doubt, he’d say what was on his mind.
When you’d get into the conversation, he’d go farther and farther, deeper and deeper. He had more uncomfortable conversations than anyone else at the company and this is why I believe he quickly rose through the ranks and was groomed to become CEO of a company that eventually sold for $50 million. He was 28 years old when that happened and started with us at about 22.
8. Be Ultra Curious For It’s Own Sake
Curiosity is arguably the best keystone trait to have when looking for hiring talent and building your culture. Curiosity precedes the asking of good questions and good questions show you care and want to learn about someone.
Curious people generally enjoy the act of geeking out about anything. I can geek out about designer fashion, fundraising strategy or anything else. I get excited to talk about how I’m reading pieces of 12 books a day and my strategy for how I read. I’ve found a good question to gauge someone’s curiosity is by asking them what books they’re reading. Curious people can go on and on about what they’re reading and why and how much they’re enjoying it.
9. To Manufacture Passionate Work, Do Something That’s Worth Dying For
“Find something worth dying for, and live for it” — Peter Diamandis
It’s hard showing up each and every day with everything you have. At some point, you’ll bump into roadblocks so doing something that makes continuing a no brainer requires it to be something deeply meaningful, that either pisses you off or brings out great joy, mastery, or passion from within you.
Something you would do anyway — for now pay.
Increase your chances by doing something you’re obsessed with that’s bigger than yourself. Something where if you’d really give your life to see that problem solved.
That’s the strong enough ‘why’ to get you through any ‘how’.
10. Don’t Make The Mistake Of “Following Your Passion”
“The trick is to become a passionate person, by embracing obstacles for growth. Not have your passion activity bring it out of you.” — me
This is a vague one so I’ll provide further context: many people believe (and I was one of them) that if they simply make their work the craft that they ‘love’ (in this context, enjoy doing), they’ll chug a long and get through the pains of entrepreneurship. However success in entrepreneurship is based on so many different things: market, product, marketing, timing, team, hiring and the list goes on actually much longer than that even.
So if you like to cook food, understand that starting a restaurant is so much different than the activity of making food. It’s managing people, expenses and mostly, marketing/PR. There’s massive risk, margins and uncertainty in market dynamics that change. So you need the proper planning and capital strategy. Those things have nothing to do with cooking of course and as much as you can hire others to do that stuff. It’s not ideal to have the most important pieces that determine success be outsourced. It’s only later on when you become a well known chef you can partner with big backers to really focus on your craft. Even then you spend most of the time on PR (just look at other celebrity chefs).
Similarly, being an artists ends up having to spend time networking to get influential people to buy and represent your work.
The activities of entrepreneurship are far apart from the passionate work itself that it makes people resent their craft after starting the passion project or start up.
11. Managing Your Psychology Is The Foundation Because It Leads To Execution
Ideas are cheap. Ideas are easy. Ideas are common. Everybody has ideas. Ideas are highly, highly overvalued. Execution is all that matters — Casey Neistat
Execution is everything.
Being deserved and entitled enough to achieve your goal is a critical principle to understand and key to your goal achievement.
This is why many successful entrepreneurs, for better or worse, are exceptionally entitled and believe in themselves wholeheartedly. This is why 23% of the United States’ millionaires are millennials. While they’re (I’m on the tail end of being a millennial) are often considered the most entitled group, it’s that entitlement that allows them to believe in themselves to achieve big goals.
This is a difficult one I’ve struggled to figure out and continue to explore it’s intricacies.
It seems at a market level — fundraising is getting harder and harder while there’s more and more money out there. I’ve gone through the process of raising seed funding for two companies, about $1.5 million in total. Not a ton of money but I’ve done the investor ‘road show’ to both seed angel investors and have pitched blue chip VC’s in SF and beyond.
It seems that raising a solid round of funding from the right people begins with your lead investor. Who’s the influencer investor that will push his/her other influencer investors to invest in your company? That’s the key to getting a nice flush round of money on your seed round and getting the right investors to come to you. This is obviously hard but as I’ve observed the landscape, there’s usually a strategic industry partner who plays a role in ramping the big seed rounds you read about unless the team is a repeat team. Exceptional examples of this are Oscar Health, Compass and Convoy. Outliers to be sure though good case studies to analyze.
13. Fundraising Strategy (fundraising continued)
Unless you’re a 2 or 3 time repeat entrepreneur, which is where all the deals investors spend their time chasing, it will be exceptionally difficult to pull off the fundraising strategy in #12. The way to do this however, is through classic discovery and selling.
Go to investors asking them what they want to do. What markets are they interested in? Every investor has a spot in their portfolio they want to fill. Often they’ll pass on you because they have a ‘conflict’ because of a similiar company in your market.
So figure out what kind of company they want to author and be a part of starting? Conceiving the idea from scratch with them is a great way to find your lead seed investors. Then make sure to have them commit to helping you. If they’re vested enough, they will. It’s all about getting and keeping them vested. You want to have that investor emailing/calling and pushing the other investors to come on. Once you achieve critical mass, the herd will follow as everyone investing loves mostly follows. That first one is the toughest.
“Great distribution can give you a terminal monopoly, even if your product is undifferentiated. The converse is that product differentiation itself doesn’t get you anywhere. Nikola Tesla went nowhere because he didn’t nail distribution.” — Peter Thiel
I see so many start ups get this one wrong and marketing is critical. I’m currently figuring this out the hard way as well. Nailing who your exact customer profile is, a long with your segment strategy and then discovering the cost effective way to reaching those people can be tough. We’re going through growing pains with it now.
The days of picking up the phone and calling your contacts are over. You need to reach deep into the market with the right tools and constantly stay in touch.
Email is king here. Email is the new prized real estate of today so winning in people’s inbox will get you far. Then of course there’s figuring out your cost per customer acquisition and finding your paid sweet spot.
My latest thinking is the best way to find the right prospects is.
15. Product Market Fit — The Moment You Know You Have Something
Great products don’t need to be sold, they sell themselves. — Richie Norton
Getting to product market fit is the most important part of any start up. Nothing else really matters and every measure should be taken to get to this point before anything else.
Product market fit is when there’s a clearly signaled need from the market for your product and people are going out of your way to bring that product out of you.
There’s a super fine balancing act with this as you the innovator want to “give people what they don’t know they want yet” while taking their feedback. It’s hard to walk that line but remember to realize signals are really clear and keep it simple.
At my first company, we were all first time start up workers going at it hard and by the seat of our pants. Most of us in our early 20’s. Clients would complain so much about how we weren’t structured enough or our inexperience was painful to them. Yet they kept buying and renewing every year. 5, 6 and 7 years in a row. Our product was so good it didn’t matter how good or bad the team was. A great product wins every time.
16. Product and Selling The Problem
“You can always feel when product/market fit isn’t happening. The customers aren’t quite getting value out of the product, word of mouth isn’t spreading, usage isn’t growing that fast, press reviews are kind of “blah”, the sales cycle takes too long, and lots of deals never close.” — Marc Andreeson
Noone cares about your product, they care about their problems. This is why enterprise sales companies like Oracle and others can sell millions and millions of product without showing any kind of product. Learning how to discover problems or convincing companies that a problem exist is the most valuable skill in selling anything. We’re currently facing this challenge at my company. Trying to clearly articulate the problem companies have and how we’re the experts to solve it with our product.
When considering your product, keep it simple. For example, people love coffee. If you’re starting a new brand of coffee, and you brought ten coffee drinkers into a room, one or two of them should want to buy your new coffee drink or bean. It’s that simple. If they don’t, your product isn’t good enough. Here are three brilliant ways to test, create and articulate a problem.
17. Allow Yourself To Be Successful By Not Expecting So Much
“Replace expectation with appreciation and watch your world change.” — Tony Robbins
Expectations set us up to not feel joyful upon achieving what we expect. Even if you hit the goal you’re expecting, you feel mere contentment and satisfaction. It may be counterintuitive but let go of expecting results on a daily basis. Work in surrender. If you do that, you give yourself space to be surprised and delighted.
I just joined a writing group and didn’t expect anything from the community. I’ve been pleasantly surprised to see how much joy they bring me with their enthusiasm and support. Had I expected “the community” in the writing group to “be supportive” all the time, I wouldn’t have allowed myself the space to be delighted. This applies to everything whether it’s goal setting or relationships.
Look to see the good and what you can be grateful for and you’ll find people will surprise you for the better. If ‘they’ go the opposite route, be compassionate and forgiving and you can help them change as a result.
I believe this is the biggest secret to happy entrepreneurship which to me is successful entrepreneurship.