7 Entrepreneurial Mindset Lessons from Founders that Raised Millions

A large part of my role at Altar revolves around having conversations with entrepreneurs. 

First and foremost, I believe good marketing comes from speaking with the people you’re trying to help as frequently as possible.

If you can combine that with a program that can bring value to the community and position your business, like our interview series, The Startup Journey even better.

And then there are the informal conversations with all the entrepreneurs whose products we help bring to life on their go to market strategies.

Throughout these conversations, the importance of having the right mindset became clearer and clearer. 

Successful entrepreneurs actively work on this mindset, consciously embracing certain characteristics.

In this article, I’ll share 7 essential characteristics of the entrepreneurial mindset that I’ve seen in the successful entrepreneurs I’ve spoken to as part of my work at Altar. 

A phrase you’ve probably heard before, the idea of falling in love with the problem, not the solution is famously attributed to Uri Levine. Co-founder of Waze. 

It’s a characteristic that is essential to the entrepreneurial mindset. Something made clear to me in a conversation I had with serial entrepreneur, Ali Halabi.

After moving to Istanbul for his corporate job, he instantly fell in love with the city. 

The only problem he had with the city was gridlock commuter traffic. 

So one year after moving, he left his corporate job and set out to solve it. 

His solution was an on-demand carpooling service – Volt. 

But Volt saw little adoption and failed soon after, never achieving product-market fit. Users didn’t want to carpool, as those driving would have to go out of their way to pick up passengers – making their commute longer and less efficient than before. 

Had Ali been focused on the solution, that would’ve been the end of the road. 

Luckily, Ali had fallen in love with the problem, so he simply pivoted to a different solution:

“The problem for me was very clear. It was traffic.

I was not in love with on-demand carpooling. I was in love with solving traffic. And that helped me to walk away from Volt and figure out what to do next. 

I ended up jumping from one end of the spectrum to the other. Having focused on C2C with my first startup, my second focused on B2B. 

I created a completely new company that focused on corporate transportation. 

That’s how Volt Lines was born. 

We help corporations offer their employees buses to work. It basically means their commute is free – it’s an added perk for the employee. 

But instead of the company buying or renting the buses (which is what they usually do) we are a subscription-based service. 

The result is that the company is not renting a bus that may end up only being half full. Instead, the employee simply uses the mobile app to access the entire Volt Lines network.”

This characteristic of the entrepreneurial mindset paid dividends for Ali and his team. Since its launch in 2017 Volt Lines has grown rapidly, achieving over $7.5M in funding – with no signs of slowing down. 

It’s a common misconception that you should keep your idea under lock and key until you release it to the world. 

However, the majority of successful entrepreneurs would tell you the opposite. 

Part of the entrepreneurial mindset is not being afraid to share your ideas and ask for feedback and help to make it a reality. 

Take Giacomo’s story as an example. He sold his startup, Moneymour, to one of Europe’s most valuable fintech unicorns, Klarna, before he’d even launched. 

Giacomo attributes part of his success to his ability to reach out to others: 

“Don’t underestimate the importance of sharing your idea and being able to ask for people’s help. 

I wouldn’t have imagined I could have so much help from the people I talked to at the early stages of Moneymour, their advice had a hugely beneficial impact. 

Let me give you an example:

Our startup incubator was extremely helpful. But not all of the startups that were part of that acceleration programme made the right use of them. 

They were not calling them twice a day. Whereas I knew I had that opportunity so I took it, and it was very valuable for us. 

So embrace that ability to ask for help, it’s one of the most valuable resources you have. You’ll be surprised how many people will be happy to help.”

But Giacomo is not alone. Wade Eyerly, who we’ll talk about more in just a moment, also shared his thoughts on this aspect of the entrepreneurial mindset when we spoke: 

“As entrepreneurs, we’ve all needed so much help to get to where we are, that we understand and most of us are still calling people looking for help! 

So when you call entrepreneurs and say: Hey, can I get 20 minutes? I want to bounce an idea off you.

The answer is: Yeah. Okay.

Every single time.”

All of this to say, there’s no such thing as a “Solopreneur” – so don’t be afraid to reach out to your network for support. 

Needless to say that creativity and the ability to think outside the box are crucial elements of the entrepreneurial mindset. 

And often, this manifests itself in asking “why not?” when others would ask “why?”.

Take this excerpt from Reid Hoffman’s Master’s of Scale interview with Sir Richard Branson as an example: 

“Hoffman: Saying “Screw it, let’s do it” is how Richard has started many of Virgin’s most legendary ventures. It’s even the title of one of his many books. 

And it fits perfectly in with my metaphor for entrepreneurship: that it’s like jumping off a cliff and then building the airplane as you fall.

 And the prelude to each of these bold jumps is the refrain: “What if? Why not?”

That’s why I believe you should never stop asking “What if?” and “Why not?” Take those daring notions seriously, and go all-in on the bold leaps. They will keep you innovating.” 

A great example of this characteristic comes from Wade Eyerly. I recently sat down with him to discuss several of the startups he’s launched. One of which being SurfAir, an airline that pioneered subscription-based flying. 

The basic idea behind the company? “All you can fly” for $2,000 a month. 

Fast forward to today and Surf Air is approaching an IPO. But the reason why Wade chose to start an airline is where I would like to focus. 

In short, he built it because his brother needed a job…

“My brother needed a job. He’s a pilot and had just graduated from Embry-Riddle.

He calls me and says: “There are no jobs for pilots. What do I do?” 

I told him I didn’t know. I’ve never had a path. I was a white house staffer. Then I joined an intelligence agency, I chased shiny things. I didn’t have a career, I didn’t know what I wanted to be. 

My brother had always wanted to be a pilot. So I asked him, “What’s it going to take to keep you in the air?”

He was young and flippant so he goes: ”I don’t know, buy a plane, start an  airline.”

I said, ok, I’ll look into it. And I hung up the phone.

We’re two kids who grew up on and off government support. So it was a pretty bold idea. It’s not like we came from money and could just buy a few planes and start flying.

Neither of us had ever built a business, I don’t think I even took a business class in college. 

I’ll forever remember I was playing flag football on a Saturday morning. After the game, we were all cleaning our cleats, banging and getting the mud out of them.

I turned to my buddy Reed Farnsworth, who was at the Federal Reserve at the time and said: 

‘Reed,  I’m thinking of leaving my job and starting an airline.’

He hits his cleats together and replies: ‘And I think you’re an idiot. Because all airlines do is lose money.’

It’s like the old joke, what’s the fastest way to become a millionaire? Start with a billion dollars and open an airline. 

Anyway, Reed and I went to brunch and we talked about it. Finally, he says: ‘Maybe there’s something there.”

With Reed’s on board, it wasn’t long before Wade and his brother had a founding team – and the rest is history. 

Had Wade not thought to himself “why not” when his brother flippantly said that the only way he could be a pilot was to start an airline, Surf Air would never have existed. 

Instead, they built a multi-million dollar company. 

Trusting your gut is, I believe, something every entrepreneur struggles with from time to time. After all, such a large part of entrepreneurship is trial and error and learning by doing, knowing when to listen to your intuition can be difficult  

That being said, it’s an essential characteristic of the entrepreneurial mindset. 

Now, I’m not suggesting that you ignore empirical data outright. Far from it.

You should, however, listen to your intuition.

Take Jan-Philipp’s story for example. I recently sat down with him and he shared how he built his startup, FitSense. 

Before founding the startup he worked in banking but was keen to work on something he could shape. 

He jumped into the startup world and started looking for a co-founder. 

Using a co-founder networking app that, in his words, “was essentially Tinder for co-founders” he met a tech founder. This founder already developed the tech needed for an MVP – he was just struggling to commercialise it. 

When I asked him about the driving force behind the decision to jump in on this technical founders idea, he told me that it was largely a gut decision: 

“I saw his profile [on the app] and I thought “He seems reasonably interesting.” 

So we met for a coffee, it was a three-hour meeting. I instantly knew I could trust the guy. 

After that meeting, I made the decision very quickly. 

I didn’t have too much to go on but I looked at the situation and thought: Ok he’s got a completely different skill set to me, we have an element of trust between us. He’d developed a technology in a space that I thought was growing.

That was enough for me, it was very much an “I don’t have children, I don’t have a mortgage, I’ve got a bit of savings so what could possibly go wrong?” intuition driven decision.”

This intuition-driven decision paid off, as his startup FitSense has since been acquired, and is now used by some of the biggest insurance companies in the world.

Any entrepreneur will tell you that building a startup is an inherently personal journey. The people who you work with become like family and for you, the founder, the line between work and life becomes blurred. 

So it stands to reason that one of the characteristics of an entrepreneurial mindset is doing whatever is necessary to help it succeed. 

I could write a whole article about this trait, but two examples stick out in my mind. 

The first comes from a conversation I had with Illit Geller. She’s an entrepreneur with over 21 years of experience building startups.

She dealt with the work-life balance of building a startup by actively including her family in the journey:

“My kids were always as much involved with my companies as any employee of mine is. 

They would know the focus, they would know what the next sale was going to be, they knew everyone in the company. 

It was the only way, in my opinion, to be successful was making sure my kids were involved and that they learned and appreciated the process with me.” 

More than that, she did everything in her power to create an environment where everyone she worked with could succeed: 

“As the CEO and founder, my agenda was to make sure that everybody was extremely happy, doing their thing and that they were supported. 

I wanted to be certain they were able to look at the problems and face them the right way.

Teamwork and collaboration is the name of the game. 

If I saw that my development team was working really hard on the next release and there wasn’t much I could do to help, then I would bake them cakes and bring them coffee – the point is there is always a way to help out!

I did everything in the early days, even though my title was CEO. 

I did quality assurance, product specs, I was looking at the design, I was raising money, hiring people. 

You name it, we all did it all.”

Illit isn’t the only entrepreneur who did everything possible to reach the next milestone. 

Another great example of this characteristic comes from Sean Yu. His first entrepreneurial journey began in Turkey, where he built a multi-million dollar fintech.

One of his strongest memories of the early days of his startup was being flexible enough to fill whatever role needed filling to get the job done: 

 “I was the closest thing to a CEO because I was the worst at coding and design.”

And I honestly think that’s what the “CEO” character is in an early startup. The guy who’s a bit of a jack of all trades and does anything needed to get the job done. Whether it’s marketing, sales, project management, being the janitor – whatever is needed to get the job done. 

I was still coding at this point but around 30% of my focus had now shifted to talking to investors and potential customers. 

Once we started getting customers I was kicked out of the development team! We had hired more developers and we agreed my time was much better spent elsewhere.

So my focus shifted to the business side of the company. Aligning the teams, looking at the business strategy, talking to potential partners, BizDev.”

He embodied doing whatever was necessary for his startup. 

But then, when he was able to onboard true specialists, he took the smart decision to step back and delegate. 

This leads me nicely to the next characteristic – humility. 

Sean Yu could have easily carried on filling every role. He could’ve taken the attitude of “I’ve been doing it myself well, why change now?” 

Knowing when to onboard true specialists and take that step back requires humility. 

But Sean isn’t the only entrepreneur who showed true humility. 

When I sat down with multi-exit founder Yaron Samid, he shared a story that also showed true humility in the name of startup success. 

Yaron is the founder behind BillGuard, a multi-million dollar fintech app that helps you save money. 

But the original idea for the product looked a little different. It was initially designed as a “set and forget” security product to protect you from credit card fraud. 

There was just one problem. Despite all the market research and due diligence that Yaron and his team did, when it came to launching nobody got excited about the product, so they didn’t adopt it. Or as Yaron put it: 

“We had to convince consumers that, without our app to protect them, they would lose money to fraud.

I asked people: “If we build a free product that would check your bills for you and notify you if there was a fraudulent charge that your bank missed; would you use it?” 

Almost 100% of people said: “I would absolutely use it, I never check my bills, I know I’m losing money. I would love something to check for me – especially if it’s free.” 

That question was a big mistake.

That kind of question is a “yes question.” 

Everybody will say yes to that. You’re not validating customer demand. More specifically you’re not validating customer action.

People had the intent, but when we launched, suddenly nobody stopped what they were doing to sign-up and use it.

There was no driving force big enough to make them take action.”

At this point, Yaron had several options. He could’ve ignored the market and carried on trying to force a product they didn’t need down their throats. 

His other option was to have the humility to listen to the market, and pivot to better serve his startup.

Which is what he did. Yaron and his team pivoted to a B2B model – attempting to sell the product to banks. 

This, however, also failed. He and his team didn’t have enough runway to weather the notoriously long sales cycle associated with banks. 

So after two years of redesigning the product to fit the B2B market, he took another step back and pivoted back to a B2C product – this time focusing on the product itself:

“This time, instead of a security company, we built a personal finance company. 

We completely redesigned the product. It was no longer a “set & forget” website. It was now a mobile app that would help you identify ways to save money and protect you from fraud. 

That worked very very well. 

It grew very quickly. Our product team did some strong product development, UX and design work led by my amazing co-founder and CTO, Raphael Ouzan. We were able to build one of the fastest-growing finance apps in history. Within a year and a half of launch, we grew to 2M active users. We were regularly ranked the top finance app in both the Google and Apple app stores.

​​At that point, we were acquired by a $2B unicorn company; while we were still growing rapidly.” 

None of Yaron’s success would’ve been possible without leaving his ego out of the equation. 

There is one other characteristic of the entrepreneurial mindset that Yaron (and almost all of the entrepreneurs on this list) personified on his journey. That of passion, commitment and perseverance.

In my opinion, this last one is a “holy trinity” for any entrepreneurial mindset. 

I say this because, from the successful entrepreneurs I’ve spoken and worked with, all three are critical to success. 

Let’s take a look at some examples. 

For Yaron, going through multiple pivots so early in his startup journey must’ve, at times, felt like hitting his head against a brick wall. 

Committing to the startup, and everyone else working on that startup and persevering through every hurdle was critical to his success. 

The same goes for Ali. After his first startup failed, he wouldn’t have tried a second time without passion, commitment and perseverance. 

For Sean, it took commitment to fill any and every role necessary. More than that, it required a true passion for his startup. 

Illit’s passion and commitment is clear in the way she fused her personal and professional life to achieve success. 

For Giacomo, it took true passion and perseverance to get other people excited enough about his company to give him their time and expertise. 

If Wade Eyerly hadn’t committed to helping his brother, and in doing so found a passion for his startup, it would never have worked (I mean, the guy built a freakin’ airline!)

The last example of this final characteristic comes from Silicon Valley veteran Garret Gafke. I recently sat down with him to discuss his experience building startups over his nearly three-decade-long career.

He faced countless hurdles when bringing his startup, IdentityMind, to life. 

It was passion, commitment and perseverance that led him to success:

 “Of course, my co-founders and I saw the lack of demand. Sure, we were told “no” a million times – like a lot of entrepreneurs. 

After all, failure is the primary denominator in the entrepreneurial process.

What it comes down to is your drive, values, and commitment.

Grit and tuning out the naysayers is critical.  You must persevere! 

You’ve got to “scrap” as I call it. 

The best CEOs and entrepreneurs I know are what I call very scrappy people. 

And what I mean by that is we work hard. 

We work incredibly hard and give everything, every piece of our being to these journeys – even if they end unsuccessfully.

More than that, scrappy people are also very resourceful. You figure out a way to work for very little money. 

The other major factor is, you and your co-founders commit to each other. 

Do not underestimate your partners in any journey, business or personal. 

When times were tough, often what kept us going was our commitment to each other as a founding team.”

As I mentioned at the top of his article, an entrepreneurial mindset is seldom accidental. 

Entrepreneurs have to actively make an effort to nurture it. 

So, finally, here are some tips to help you develop and nurture your entrepreneurial mindset:

Many see failure as a bad thing. And it is. But is also one of the greatest learning moments for founders.

My co-founder, Paolo, always says: 

“If you launch your startup and no one adopts your product, it doesn’t mean that you’ve failed – far from it. You’ve learnt that, in its current state, it doesn’t truly solve the problem you set out to solve. 

Now, you have the opportunity to gather feedback from the market and try something new.

A true failure would be never trying in the first place.”

Set clear milestones in every facet of what you do. Write them down, tell your family and friends about them – so you can be held accountable. A mentor or coach can also help a lot here. 

Once you have clearly defined your milestones – that neverending list of things to do will seem a lot more manageable. 

Curiosity is a superpower for entrepreneurs. Continually look at the world around you and ask questions. 

Why did you end up waiting in line so long at the supermarket? Could you create something to make the process more efficient? 

Why did that entrepreneur you connected with on LinkedIn decide to build his startup that way? What gave him that idea? 

It’s like Wade Eyerly told me: 

“I often tell people that a good entrepreneur is like a good screenwriter.

The screenwriter has a dozen half-written scripts in their drawer. They pull it out and they write the 30 pages, but it’s not done. 

I feel like good entrepreneurs are the same way. It’s not just one thing. It’s all the things.”

As important as it is to look at the world around you, you also need to look inward. 

Try to constantly revisit your vision, look at it objectively, decide if it’s still relevant for the market you intend to serve. 

This is one of the best ways to keep your startup on track.

As we’ve seen from the examples above, there’s rarely only one way to solve a problem. 

Practice looking at hurdles from every angle. Entrepreneurship is chiefly trial and error – so don’t be afraid to explore different angles. 

The last step in nurturing an entrepreneurial mindset is to always ask yourself “How am I providing value?” 

This starts with the product you’re building. How does it provide value for your users? Can it do better? 

Next, how is your startup providing value not only to your users but also to those who work with you? How can you do more? 

Finally, how are you providing value to your startup? What can you do to drive your startup forward to its next milestone?

Thanks for reading and please enjoy the ride. 

Also Published Here