Lessons These Entrepreneurs Learned From Tough Business Situations - Rolling Stone
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Eight Lessons These Entrepreneurs Learned From Their Toughest Business Situations

You can’t grow your business without facing a few obstacles along the way.

Photos of the featured members.Photos of the featured members.

Photos courtesy of the members.

Opinions expressed are solely those of the author and do not reflect the views of Rolling Stone editors or publishers.

Leading a business often comes with its own unique challenges, some more difficult to navigate than others. What separates great leaders from good ones is the ability to face those challenges, overcome them and come out stronger and wiser on the other side. No matter the challenge, there’s always a lesson to be learned that can either overwhelm you or help your business grow.

But learning those lessons can often be a challenge in itself. Below, a panel of Rolling Stone Culture Council leaders detail the lessons they’ve learned from some of the most difficult business situations they’ve faced and how they became all the wiser for it.

Invest in Tech That Allows You to Scale

In 2014, we had an outage due to the scale of new business and the number of users accessing our server. Three days and nights of work later, we fixed the issue and created a plan for the future. Since then, we’ve made further investments in our architecture and hosting. I learned to invest in the tech and hosts that will allow us, and our clients, to successfully scale, which other providers haven’t. – Jessica Billingsley, Akerna

Separate Business From the Personal

The most difficult business situation I’ve ever been in was having to lay off a friend. They were understandably upset, and it’s never an easy thing to not take personally. It was the beginning of me learning how to separate business from my personal relationships and how to make difficult business decisions with compassion. – Sara Payan, The Apothecarium

Being a Leader Sometimes Means Stepping Away

The most difficult business situation I’ve ever been in was when I got a call from my sister that my mum was at the end stage of her life. This meant that, right in the middle of Covid, I had to literally drop everything and jump on a plane to Australia. I had to spend 14 days quarantined in a hotel before being able to spend 11 days with my mother before she passed. During that time, I had to physically and mentally step away from my business. I couldn’t fathom working or being in the right mental space to be present, and should one of my team members have gone through the same thing, I wouldn’t expect any different. This time also allowed my leadership team to step up and make decisions without the safety net of my presence. It was a time of growth for all of us. – Ginni Saraswati, Ginni Media

Update or Be Obsolete

A recently pressing issue has been the digital tax for streaming services that has been added worldwide by country. To overcome this, we have had to modify our software to include a tax line, and inform our customers of a three percent minimum coming off the top of their revenue. Evidently, governments will do what they want, and tech companies, such as Aux Mode, have no choice but to update or be obsolete. – Adam Rumanek, Aux Mode Inc.

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Document Processes in a Scalable Way

Not documenting processes in a scalable way stifled our agency early on and created unnecessary internal frustrations with staff. Hiring an outside project manager whose only focus was to create a playbook resource for both our team and clients was a game-changer. The playbook documents every process and has allowed us to grow and service our clients better than ever before. – Danielle Sabrina, Tribe Builder Media

Find a Business Model That Works for You

The most challenging business situation I’ve been in was when I had to make the decision to shut down my first business, which was a fashion website I made in college. It was my first jump into entrepreneurship, and I learned quickly that an inventory-based business is very costly if items don’t sell. It was sad to say goodbye to my team, our warehouse, our customers and the dream I had that this business was going to be a home run for me. Ever since, I’ve made sure that any company or project I’ve been a part of has not been inventory-related and has been more tech-focused instead. – Vanessa Gabriel, Drop Delivery

Listening Is Often the Best Solution

I was charged with leading the integration of a distressed company into my business unit. It was a group that had been through a year of budget cuts and uncertainty, and there was distrust with the new regime. I went on a listening tour to hear their concerns and their ideas. It created a foundation of trust that engaged and energized the collective team and set everyone on a path for success. – Michael Klein, Miraculo Inc.

If You Don’t Trust Someone, Walk

I said “no, thank you” to $20 million for all the right reasons. A long-time colleague set up a meeting with a funder for a film, who ended up bringing someone unexpected at the last minute. They tried pressuring us and changing the deal to their advantage from what was already agreed to. Most importantly, they couldn’t give a straight answer to simple questions. What I learned is: If you don’t trust someone, walk. – Susan Johnston, New Media Film Festival®


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