Kathryn Minshew was rejected 148 times before raising nearly $30 million for The Muse.

Marc Benioff couldn’t raise a single dollar from venture capitalists—many of whom were his friends. And yet, Salesforce raised over $60 million from private individual investors before going public in 2004.

Reid Hoffman and Allen Blue stated investors simply didn’t buy into their initial vision for LinkedIn. The fact that they were immediately amassing scale over revenues did not go over well with VCs.

Meanwhile, when Niniane Wang, Susan Ho, and Leiti Hsu went to raise money for Minted and Journy, they grappled with inappropriate advances from their audience.

Each of these founders faced their fair share of adversity. And in spite of that adversity, they relied on a key asset—grit—to make their visions a reality.

You Need to Believe You’ll Make It

Self-belief is a powerful source of grit.

Growing up with two brothers and a single mother, life was very difficult at times. I definitely faced my fair share of adversity—in fact, I became a breadwinner early so I could help put food on the table.

But it made me tough. When things seemed bleakest, I knew that one day I would make it.

Fast-forward to a billion-dollar tech transaction I was running last year: I was leading the messiest diligence process of all time. The company I was advising endured a lot of turmoil, and putting together materials for an interested buyer was often an afterthought. I was on the ground, dragging this transaction kicking and screaming to the finish line. For weeks on end, this meant skipping meals, working for seemingly endless stretches, and getting three hours of sleep each night.

And again, I knew I’d make it through. I knew that I had survived days of not knowing where my next meal would come from—of not knowing whether there would be a roof over our heads the next week.

This transaction paled in comparison. It was easy, as crazy as that sounds. As such—thanks to the toughness I developed as a kid—I knew I would make it through this deal.

And I did. I helped a founder sell the company he started a lifetime ago. I helped him realize his longtime vision. He faced scrutiny from all directions, and it was a long and arduous process, but we made it—and I knew we would.

You Will Deal with Difficult People

If it were easy, everyone would do it.


It’s not easy—and people will jump at the opportunity to get in your way.

I recently helped a social commerce founder raise seed funding and get accepted into a highly-selective female-focused accelerator. Out of 100 applicants, the company was one of only three selected. Along the way, the founder was constantly told she would never make it. Despite top-flight brands lining up for proof-of-concepts, investors didn’t hesitate to dismiss her vision.

Today she’s transforming eCommerce and blazing a trail in helping brands develop user-generated content.

Similarly, for the first eCommerce company that I launched, my initial investor pitches went well.

Until they didn’t. I had investors tear up my business plans and explain at length how my vision wouldn’t work. It was admittedly discouraging, but after licking my wounds I committed to making an even greater effort.

As a result, I aced my next pitch—and the one after that.

When I was worried an elitist landlord was going to evict my family, I didn’t fold. I worked my butt off that summer to help pay the bills. Then I lugged cardboard boxes past 3 a.m. to move into a better home.

You need to expect that there will be difficult people along the way. Take the dirt they throw in your face as fuel, and use it to keep working toward achieving your goals.

You Have to Pull Out All the Stops

I had the pleasure of advising another female-founded eCommerce and artisan brand that recently raised seed funding. The brand is predicated on high-quality ingredients.

When blue-chip companies partner with the founder, they’re also putting their reputations on the line. So when it came to sourcing raw materials in Vietnam, the founder didn’t just take the suppliers’ word for it being a good fit—she got on a plane and flew there, and trekked her way through the Vietnam countryside to see it with her own eyes.

Similarly, when I was helping a young company get off the ground a few years ago, we had to pull out all the stops. There was no alternative.

We were up before sunrise fulfilling orders. By the time everyone else woke up, we were out pitching new clients while making deliveries to our existing clientele. And when those pitches led to new orders, we’d spend the night meeting the increased demand.

We did this day in and day out. We pulled out all the stops because we had no choice but to do so. This was a crucial phase in the early days of the startup. We couldn’t take shortcuts in laying the foundation of a young company.

We had to be relentless. We had to give it our all. And so do you.

Keep in Mind It’s All About Perspective

You need to take things one day at a time, step by step. When I was leading my first billion-dollar transaction, I pulled three all-nighters in one week—but I didn’t look at it that way.

Rather, I put things in perspective and honed in on what we needed to do in the short term.

Consider this: When I first started lifting 300 pounds at the gym, I didn’t think of it as a full set of 20 reps. I simply focused on making the next lift.

And when I ran my first race and my lungs were burning—when my legs hurt and the blisters set in—I didn’t think about the remaining mileage. Instead, I focused on the next block, and then the block after that.

I was helping a men’s lifestyle brand raise capital a few years ago, and it was a daunting process. The company had no FP&A team, no management presentations, and was still perfecting its strategy.

We didn’t look at how daunting the task was in aggregate, though. We took it one day at a time.

So I rolled up my sleeves and became the company’s one-man FP&A department. Microsoft Excel became my second home. We pitched one investor at a time, and refined the pitch as we went along. We managed to clarify the strategy and attract an even greater pool of potential investors. The team was initially discouraged, but eventually we picked up momentum.

The takeaway here is that the path ahead is never quick or easy. Simply take it one step at a time, and focus on making the most of each step. You’ll have arrived at the finish line before you know it.