Top Entrepreneurs Share Their Biggest Challenges As A Founder

Life as a founder is always filled with challenges, the key is to rise above those challenges and not let them impact your ability to reach your goals. I asked six founders what the biggest challenges that they have faced so far in their entrepreneurial journey have been.

Taylor Lindsey of CustomerSpec
“Developing a sound sales strategy on a limited budget. Understanding where my time is best spent in terms of sales, ie. finding and building relationships with industry influencers, cold calling, lead gen, marketing, etc.”
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Evan Weselyk of Ghost Pay
“The two biggest challenges for me have been proving myself as a founder without prior experience in payments and building my team.”
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Matt Holtzman of goMkt
“At goMkt, we’re creating a market that doesn’t exist to tackle the problem of food waste in the United States. Oftentimes, we encounter food businesses owners who are stuck in the old school paradigm that food waste is a built-in cost of doing business (supermarkets, for instance, optimize to stocking in products rather than risking empty shelves), and sometimes have little interest in challenging preconceived ideas. We try to show them that we’re creating an additional channel for them to rotate inventory, perform a social good, and improve their bottom line, but some of them need to see all of their competitors using an established product before they’ll even consider it, so that’s quite difficult. Nonetheless, there are enough forward-thinking food businesses so that we’ve been able to carve out a niche for ourselves, and we understand that we have to keep our eyes on the long game.”
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Shahin Arefzadeh of Ziotis
“One may have done a lot of crazy things in life, but nothing really prepares you for entrepreneurship. You have to jump in cold water and start swimming while you are putting on the swimming suite. And there is no way back. While many probably think money is the biggest issue, I believe self-awareness was (and still is) the big one for us. Understanding who you are and how resilient one needs to be, was a big lesson learned. Dealing with daily/weekly/monthly breakdowns can be lot easier then.”
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Andy Daidone of ThePresent
“Each challenge you encounter as an entrepreneur represents its own unique opportunity to learn. Whether it be pitching to investors for the first time, navigating policy or regulation, or finding product-market fit, there are countless ways you’ll be tested. With that said, the greatest challenge I’ve faced personally has been the psychological adjustment of venturing out on my own. This is an ongoing battle each and every day. You’ve taken the leap and put yourself out there for the world to see — and that means both the successes you achieve and the failures you endure. If something goes wrong, you and you alone are accountable. It’s your decisions that determine the fate of your business. There’s a constant race against time with regard to your company’s burn rate versus traction and progress, and this sits in the back your mind every day. It’s lonely most of the time. That often gets overlooked, but it is. There are crazy highs and what seem like catastrophic lows — often in the same day. But staying true to your vision, surrounding yourself with the right people, and constantly reminding yourself of why you’re doing what you’re doing have been instrumental in managing this challenge.”
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Julie Clark of Capa Talent
“I had so many challenges. It´s hard to pick just one. I guess one of the hardest challenges was hiring friends. I had helped a friend out that lost their job and it felt good to help someone in need. It ended up being a disaster though. Everything the friend complained about with their last employer ended up playing out again, but this time with me. When things unfolded, it was hard to not take the situation personal. The funny part was that my background in HR prepared me for these situations and taught me how to prevent them. But for some reason, I put down my guard when hiring a friend and overlooked any red flags I would normally would see.”
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