Welcome to 10 entrepreneurial mindsets for overcoming challenging times, featuring inspiring founders who have built successful product businesses.
As entrepreneurs, we all face challenges, from market downturns, financial pressures, and team dynamics – that can make us feel like giving up.
That’s why I created this series – to provide you with inspiration from 10 founders who have faced similar challenges, and come out on top.
You’ll meet founders who have overcome near-bankruptcy, fierce competition, and changing market trends to build businesses that generate millions of dollars in revenue, some even beyond $1B exits. Each founder will share the mindset that helped them overcome their challenges and achieve success.
As Reid Hoffman once said, “It’s going to feel like blood, sweat, and tears no matter which business idea you’re pursuing.” And as Nelson Mandela once said, “The greatest glory in living lies not in never falling, but in rising every time we fall.”
So, get ready to be inspired by the stories of these amazing entrepreneurs and learn how you too can endure and overcome challenging times with the right mindset.

#1: Grit for at least 2 years

Ft. Twitch $970M exit. Michael Siebel nearly went bankrupt with justin.tv before pivoting to Twitch, turning it into a major success with a near $1B acquisition by Amazon.

Michael Siebel explains that what fuelled his entrepreneurial mindset overcoming challenging times was relying on an extremely talented software team, trusting that this software team could deliver better software than anyone else. Plus having the patience, and grit to be willing to give a problem at least 2 years. If you are not willing to give a problem two years, you probably shouldn’t work on it at all.

#2: Shit Sandwich

Elizabeth Gilbert, best-selling author of ‘Eat, Pray, Love’ and ‘Big Magic’. Over 10M copies sold. Gilbert believes that every pursuit, no matter how exciting, comes with a ‘shit sandwich’ – a tough and unpleasant experience that one must endure. She emphasizes the importance of asking yourself, ‘What do I love so much that I don’t mind eating the shit sandwich that comes along with it?

Elizabeth: “The idea is that every pursuit, no matter how glamorous it may seem, no matter how exciting, it feels to you, no matter how much you feel like you were born to do it, comes with a shit sandwich. And so the question is not, “What do I love?” The question is, “What do I love so much that I don’t mind eating the shit sandwich that comes along with that thing?” So for me in my life writing is the thing that I love and the shit sandwich was the 7 years that I was not getting published and that I was coming home from my job as a diner waitress, as a bartender, as an au pair, as a… somebody who worked in flea markets, as a cook, and I was coming home tired and smelling like other people’s french fries, and sitting down and doing my real job, which was to write. And then to go to the mailbox the next day and get another rejection letter. And then say, “Do I still wanna do this? Because this shit sandwich sucks.” Am I ready to take another bite? You know? And I did still wanna do it and now even as somebody who makes their living as a writer, there’s no end to the shit sandwiches. It’s like, “Um, oh, hello horrible review in prominent newspaper. That’s your shit sandwich today, Liz. You still wanna do this work?” Yup. Yeah, I still do. Still worth it. Like, hello awful comment on social media from somebody who thinks you’re a pile of dog shit. You know? And just has, like, chosen every possible way that they can just cannot get it out of their system fast enough how much disregard they have for your entire life. Yup. Still wanna do this thing? Yeah, I still wanna do it. You know, so that’s the question. Because if the first time you encounter the shit sandwich you’re like, “Well, this… this isn’t worth it,” then that’s not the thing you’re supposed to be doing.

so that’s the question. So if you go into this thing thinking, “If I follow my bliss and I live my dream and I stand in my truth, then everything will be great,” it doesn’t mean everything will be great. It just means at the end of the day when you check in with yourself and you go, “In the end, on the balance, is this still better than not doing it?” And the answer is still yeah, this thing is still better than not doing it, then you’re on the right path.”

#3: Embrace Co Founders Misery

Meet Patrick Collison, co-founder of Stripe, a company with over $50 billion in revenue.

Patrick emphasizes the importance of preparing for tough times with your co-founders, not only in case of failure but also in case of success.

He acknowledges that conflicts with co-founders will cause misery, and that the key to overcoming these challenges is to communicate more openly.

Patrick: “When you look at top-tier companies and the trajectories they followed it’s pretty rare that the co-founders remain together right and it’s freaking stressful.

The thing that I wish I had better understood when we started stripe is when you start a company that’s if it doesn’t go well, if the product doesn’t work, or if you don’t get the traction you want, so it’s going to suck. You’re going to deal with all these problems, you’re going to be miserable and it’s going to be a tough time.

But what nobody tells you is if it works the flip-side is that you’re also going to have all these problems and you’re often gonna be miserable and you’re going to be putting out fires.

So actually you’re guaranteed misery instead of I either pass and so in that sense you’re also25:45 guaranteed to co-founder strife but there’s going to be significant problems to be solved and tension and challenges.

Having had before we start stripe almost twenty years of experience of resolving disputes. Hopefully our mechanisms for doing so became a little bit more sophisticated or at least a little bit more verbal over time.”

#4: Follow your Calling and Keep Trying

Abhi Ramesh, the founder of Misfits Market, who crossed $250M in revenue, initially failed in his attempt at entrepreneurship.

However, he listened to his calling and decided to give it another shot, which ultimately led to building a $1B valuation business.

Abhi’s story reminds us of the importance of following our passions and not giving up, even in the face of failure.

Abhi: “What was painful for me was being on the investor side of the table. We met management teams of these incredible companies that had scaled from zero to, you know X over the course of 3 or 4 or 5 years. The misery for me was less so I hate my job. It was more so like, “My job is fine I really want that guy’s job. Like, that’s really what I want to be doing.”And I’ve, you know, I’ve tasted enough of it. I tried this in college. I tried this in high school. They didn’t quite work. But like, I have the foundation. Now, I have a finance background. I understand how to code. I’ve tried a few things a few times and failed. Like, I think that I need to take a crack at this again.

#5: Pick the More Challenging Path

Jess Lee is the former co-founder and CEO of Polyvore, now partner at Sequoia. Her advice for overcoming challenges? Take the more challenging path, because that’s where growth happens.

Jess: “When I look back on my life and I think6:14 about all the times I had to make a difficult decision between two paths I always tried to pick the more6:19 challenging path because at least I would learn something and I would grow even if I failed so I would encourage you to pick the more challenging path that feels kind of once-in-a-lifetime. You should grab that because oftentimes the other path will still be available to you in the future.”

#6: What’s the Point of Getting Stressed?

Dara Khosrowshahi, CEO of Uber, has a pragmatic approach to stressful situations. Having witnessed his father losing everything and rebuilding his career, he developed a mindset that being stressed about disappointment or failure is not constructive.

Dara: “My family were immigrants we lost everything when we came to the states uh it crushed my dad he you know he built his whole career and it’s a little twisted which is – I’m super competitive, I work really hard, but seeing one losing everything and then rebuilding it because we were lucky enough to come to the states. So losing everything and always having my family around me and then losing everything and seeing it Crush my dad has created this weird circumstance for me which is like – worrying – it doesn’t help. Getting stressed out there’s nothing constructive about getting stressed out. Either you’re gonna fail or not fail. You’re going to make a good decision tomorrow a bad decision like why the hell stress about it? So my wife calls me a robot because I’m just able to deal with challenging situations by saying: hey this is this really sucks okay what do we do, and I’ll do my best. And with my family by me, it won’t let anything get the best of me.

#7: Failures are Stepping Stones

Failures as stepping stones to success, featuring Charlie Muirhead co-founder of CogX, $5M in Revenue.

Charlie: “Failures are just a stepping stone along the path to success and failure can be one meeting it could be the great resignation, people stepping down from your company, sometimes it’s got something to do with you sometimes it’s nothing to do with you but these little setbacks happen every single day and you have to just build up this rhino skin and this kind of imperviousness to it and if you do that whether you want to call it grit or determination i think you’ve got a huge chance of success.”

#8: Every Failure is a Connection to the Next Big Thing

Maxx Blank of Triple Whale, Raised a $25M Series B: Every failure, every mistake is just a connection to the next big thing.
Maxx: “Entrepreneurship has been. An amazing journey. And to have the context of life, life is a journey. And when you think there’s a mistake you made you realize that it’s really just a connection to the next big thing. And if you’re failing, you’re constantly picking up a learning opportunity from it”

#9: Lot’s of NO’s lead to Yes’es

Alexa Grabel, co founder of Pocus, which raised over $23M is reminding us that if you experience a lot of NO’s, and learn from these NO’s, practicing a growth mindset, and thinking through – how could you have improved your pitch, value proposition, or sales approach, you’ll eventually get the YES’es.

Alexa Grabel: “So there’s a lesson I would say that’s similar for founders and salespeople that I’m wondering if you relate to as well, that something I needed to learn and keep reminding myself is that a lot of NO’s will lead to a lot of YES’es.

So hearing NO’s whether it’s about a customer deal or anything else, it’s you have to have the growth mindset to say how can I learn from this? Is it something I could have done better? Is it product feedback? Is it positioning? And then using that to inform your lessons going forward until you get that.”

#10: Develop Thick Skin

Ft. Bryan Clayton of Greenpal, $30M Revenue 2023: Bryan learned to develop a thick skin when he started selling lawn-making services by going door-to-door. He realized that no matter how good the service was, there would always be people who would not be pleased. He learned to move on and focus on the majority who were happy with his service.

Brian: “got the doors slammed in my face. But learned a valuable lesson. Learned how to sell. Learned how to develop thick skin, and how to do that the hard way. And, and that was something that the business taught me that I never would have learned otherwise. And you learn early on that there’s probably 5% or 10% of people that no matter what you’re doing for them, you’re not going to please them and you just have to move on. That’s all you can do. And I learned that at a very early age. Looking back 20 years in business, the business has always been the thing caused me to learn lessons that I never would learned.”

#11: Be Resourceful

Andrew Horn, Co Founder and CEO of Tribute, who crossed $1M ARR, overcame near bankruptcy, by taking a job to continue funding his dream product company.

Andrew was struggling with sustaining both his family, and the flattening revenue of his company, and faced a difficult decision how to keep the company alive. So he took a job to continue funding his product.

Andrew: “The biggest challenge was being involved in a company that my co-founder and I loved very much, and seeing that company was having a hard time scaling. It’s, we had a foundational, baseline of revenue, we’d always been making money. But, as we continued to go into years three and four and the company revenue was flat and not really growing, we had a very hard decision to make, which is do we keep going with this thing or do we sunset it because it’s not looking like it’s gonna be able to pay us the type of money that we need to sustain families in New York City. And ultimately what we decided is that like we love this thing. We still think that there’s a lot of potential, there’s products to be built. And so we kept going with it during these challenging years really as a side hustle. Both my co-founder and I got jobs for two years on the side him at Google, me as an executive coach. And in that time what ended up happening is we made the product fundamentally a lot better. And then when Covid came around, we were ready for it and we were able to take advantage of that opportunity.

I love the quote from the book Peaks and Valleys: “How you manage your valleys determines how soon you reach your next peak”.
I hope this content has been helpful to you to be able to manage and endure some of your valleys.
I’d love to hear from you, whether you’d like more content like these about the character and mindset of entrepreneurs journeys, please reach out or comment below.