Success Through Risks and Mistakes: C-Suite Executives Insights

Success Through Risks and Mistakes: C-Suite Executives Insights was originally published on Ivy Exec.

Success seldom comes easy – and it’s often only found after forging forward through tough times.

Many successful C-suite executives have first found themselves in rough waters, on tough terrains, and along bumpy roads. That’s because they took risks and, sometimes, made mistakes. But those risks, over time, eventually turned into rewards, which is why they’re invaluable.

Here, we caught up with executives across various industries to learn more about some of the risks they’d taken and the lessons they’ve learned that have led them to where they are today: the C-suite.


Five lessons from C-suite execs


It wasn’t smooth sailing for all successful executives. Here are five pieces of advice about taking risks, making mistakes, and moving on to something bigger and better from folks who have done just that.


1️⃣ Investing before there’s success can breed success.

“When it comes to business, there’s no guarantee of success,” says Aktug Dogan, the CEO and co-founder of ReferMate.

“My co-founder, Bright Williams, and I both knew that when we decided to build ReferMate together. We began by investing $500 each in 2019, and it is a testament to understanding the power of careful risk that ReferMate has achieved the scale that it has since then, having processed over $13.6M in sales alongside our business partners.”

Now, Dogan and Williams have been exploring how to raise outside capital to scale even further and grow its user base, but it’s only achieved the success it has thus far because it took the risks of investing in it themselves first. 


2️⃣ Hiring the right people boils down to a gut feeling.

“The biggest risk I have taken is the selection of my team,” says Zornitza Stefanova, the CEO, and founder of BSPK, a SaaS platform for digital curation and personal shopping.

“Hiring the right people for the team takes a lot of effort, time – a gut feeling. It’s not an easy choice, and you don’t really know if the person will blend in with the team or have the same company culture.”

Learning how to listen to her gut when it comes down to hiring talent has been the most significant learning curve for her, and she tells Ivy Exec that she is happy to say that she has learned a lot.


3️⃣ Sometimes, you need to be your own advocate.

Maria Shriver, co-founder, and CEO of MOSH, a mission-driven company that educates consumers on how what they eat and drink impacts their mental and physical health, didn’t have such a simple start.

She founded her company after witnessing her father slowly lose his mind to Alzheimer’s. She wanted to create health-centric markets that contained the supplements needed to benefit the brain.

“However, many companies I pitched my vision to didn’t seem convinced that an idea brought to them by a woman in her 60s would be viable in today’s marketplace,” she says. ‘Additionally, no one I spoke with understood the importance of eating for brain and body health, so they felt consumers wouldn’t be interested either. But my experience within the Alzheimer’s space knew otherwise.”

She launched MOSH anyway, “changing the zeitgeist of how people think about brain health,” she adds. And she sold 1,000,000 bars within her first year in business.

“As an entrepreneur, it’s vital to keep your momentum going by pushing through those challenging moments,” she explains. “Not everyone will have the same passion for your vision as you do. So being persistent in your efforts is crucial, as you’ll gain more knowledge and confidence by taking the hard road instead of the easy one.”


4️⃣ High risk means high reward.

“While bootstrapping enables me to grow my business on my terms, it also means taking on all the financial risks myself,” says Dan Kroytor, the founder and director of TailoredPay, a merchant account provider which specializes in high-risk card processing services. “But this comes with a real sense of reward.”

Not taking on any outside financing allows his company to do what’s best for its customers instead of the investors, he explains. He considers it a more authentic way of doing business in a marketplace that he says is oversaturated with angel investor-backed startups.

“Because our client list includes many high-risk merchants… it’s an opportunity for us to help democratize entry into the e-commerce space,” he explains. “For these reasons, we view risk-taking as vital to disrupting the way businesses operate.”


5️⃣ Change can be scary but necessary.

Brad Hall, co-founder and CEO of SONU Sleep had to take quite a leap to get to where he is today.

The two greatest risks he tells Ivy Exec that he took were switching careers and starting his own business

“Changing industries partway through my career was a risk that many people are hesitant to take for fear of backtracking, but doing so brought me to the position I’m in today,” he explains. “While starting your own business is a hugely daunting and complicated task, watching my idea change the industry and improve the lives of my customers has been worth every challenge and struggle.”

For more advice on taking risks, check out Ivy Exec’s resources on everything from taking risks without losing it all to, more specifically, taking risks in a shaky economy.

You can also check out a webinar on Ivy Exec on how to deal with uncertainty and risk as a leader. 

Ultimately, remember that mistakes are meant to be made. But also remember to learn from those mistakes.

By Ivy Exec
Ivy Exec is your dedicated career development resource.