8 Entrepreneurs Talk About the Biggest Challenges They Faced in Getting Their Startups Off the Ground
Welcome to Recruiter Q&A, where we pose employment-related questions to the experts and share their answers! Have a question you’d like to ask? Leave it in the comments, and you might just see it in the next installment of Recruiter Q&A!
Today’s Question: The entrepreneur’s life is not an easy one. It’s difficult – if not downright impossible – to find a single entrepreneur who didn’t have to overcome innumerable obstacles in order to make their business dream a reality. We reached out to a few entrepreneurs and asked them to share their stories about their toughest challenges.
1. Maintaining a Healthy Work-Life Balance
The biggest challenge I overcame as an entrepreneur was finding work-life balance – more specifically, finding it with a significant other. There is no denying the time, work, and stress that are inherent in building a startup, but one of the most misunderstood facets of the entrepreneurial lifestyle is the psychological burden you feel even when you aren’t actively working. Everything I see, hear, or discuss in some way makes my mind drift toward Beatactive. I always have ideas and to-do lists churning in my mind, morning, noon, and night.
When you want to enjoy time with your significant other – especially if you live together – it can be a massive challenge to be present in the moment and give your undivided attention to them without drifting back to your business. Fight after fight riddled my relationship as it grew more and more obvious that I wasn’t focusing my emotional and psychological energy where it should have been: on my loved ones.
The greatest tool in an entrepreneur’s personal tool box is the ability to turn off your startup brain and turn on your real-life brain. In a more tangible sense, simply turning my phone completely off – not just putting it on silent – works wonders when it comes to overcoming my mental startup factory and enjoying my friends, family, and loved ones.
In hindsight, I realize that I took a risk by starting a business, Unwrap, that wasn’t solving a problem I had experienced firsthand. While it had some elements of being mission-driven in terms of enabling business owners to connect with their audiences on these new social platforms, we were very reactive. The business was making money – we had millions of users – but it was unclear what long-term goal we were building toward. It felt like something was missing.
We didn’t have a clear purpose that could guide us over the coming few years, let alone the subsequent five or 10. I realized that if we were going to grow the team, I wanted to be able to speak about our goals in a way that I’d be able to repeat them a thousand times and have just as much passion and conviction as the first time. So, even though we had funding available to us, we ended up accepting one of the acquisition offers we had received.
While I learned a lot from the experience, the business was a clear contrast to the mission-driven mentality at my current company, Gusto, where my teammates and I strive to do the best work of our lives every day.
As an entrepreneur, my biggest challenge in building a successful start up was me – my propensity to get sidetracked onto something new. There are always opportunities to be discovered and concepts to make into realities. But timing is key, and sometimes, I get attracted to the next venture before we have properly established the one on which we are currently working.
I overcome my own deficiencies by surrounding myself with an outstanding company of people. They are the reason for the success we have had in starting our businesses and developing our manufacturing technology platforms. An entrepreneur who thinks it can be done alone is on a crash course with failure. Outstanding people are needed.
The financial struggles have definitely been the most challenging aspect of my business. Coming from a career where I made nearly $120K a year, living a pretty fabulous life traveling, dining out, and shopping like it was my job in one of the most expensive cities in the world, I came up with an idea that I had to bring to life. In May of 2010, I launched Cheekd.com.
After finishing off my savings from my 15-year career in architecture, I had to get extremely creative to continue funding my business, and this is where the financial sacrifices began. I made nearly $75,000 by selling my designer clothes at consignment shops and on eBay, doing focus groups, secret shopping, and by selling my electronics and other odds and ends around my apartment on Craigslist. All the money went straight back into my business. The biggest chunk of cash came from renting out my West Village studio in NYC on AirBnB while couch surfing for 14 months. I nearly got evicted and ultimately lost my lease of five years in my gorgeous apartment.
Finally, after four tumultuous years of building my startup with the wrong partners, lots of bad decisions, and some major rookie mistakes, I was determined to find a way to take my business to the next level. What better way than to apply to ABC’s Shark Tank?
In September of 2013, I found myself walking down that scary shark-infested hallway and into a stare off with five of the harshest millionaire investors in the world. I’d never been more nervous in my entire life. When I proclaimed I was going to change the population with my reverse-engineered online dating business, serial entrepreneur and Dallas Mavericks owner Mark Cuban rolled his eyes, called me delusional, and immediately snapped, “I’m out.” Billionaire investor Kevin O’Leary demanded that I quit my “hobby” and shoot my business – my passion – like a rabid dog.
In the 48 hours after the broadcast, Cheekd.com received a record-breaking 100K unique visitors, and our inbox filled up with thousands of emails insisting that the “Sharks” were “out of their minds” for not investing. A little under 50 of those emails were from interested investors. Since that episode of Shark Tank aired in February of 2014, I have found the missing links from years before. We’ve raised five times the amount I’d sought on the show, and I’ve gotten a CTO on board who has helped facilitate and finance the new face and technology behind the new Cheekd.
The biggest challenge I personally overcame to become a successful entrepreneur was getting my fellow employees to have the same amount of faith and trust in my startup as I did.
I started my company, Efficient Home Services, in 2011, with nothing to my name outside of a vision. The biggest challenge was having so much ambition and belief in my company and trying to convince others to work for me – people who weren’t sure if we would succeed or not.
I overcame this obstacle by constantly keeping a positive attitude and not allowing my employees to stress when things weren’t going right. If money was tight, I would pass up my paychecks to make sure my employees were taken care of. This, over time, helped my team learn to trust in me and my company and share my vision.
Now, five years later, business is doing so amazingly it is hard to keep up at times! I used to have to beg people to work for my company, and now I have people begging for the opportunity to work with me.
I started my business, Bedford Executive Search & Consulting, at the end of 2011. Having worked for some rather large corporations, I found that I needed to retrain my brain to think differently, more like an individual contributor across many functional areas. When you go out on your own, you lose the comforts and support that a larger organization can provide.
I’ve always been someone who liked to figure things out on my own. In a few months’ time, I found myself wearing many hats in the space of a day, from IT troubleshooter to graphic designer to bookkeeper to sales person to public relations aficionado. It was overwhelming and made me wonder if I’d made the right decision to start my own HR recruiting and consulting business. I was putting in 15+ hours a day and still felt as if I was falling behind. It was then that I realized I needed help – but I didn’t have the money to hire people yet.
So, I became creative. I reached out to friends who were subject matter experts in these areas and asked if they would be willing to offer consultation to steer me in the right direction. I contacted other startups in the areas I needed expertise and offered my HR expertise in exchange for theirs. Not everyone was open to the idea, but some were. I guess you could say I bartered my business skills for theirs in order to grow my business on a shoestring budget. And it worked.
Don’t be afraid to get creative and seek advice or support. There are others out there just like you, plugging away and trying to do it all. And you don’t need to do it all – but you do need to ask for help. It’s the difference between working hard and working smart.
While I knew I was capable, I was insecure about others viewing me as such without any track record. I was also concerned about how long it would take to build my reputation. I had no money to speak of, so I would not last long without referrals. I just went for it.
The first referral is always the hardest, and, for me, it just came out of the blue. It seemed like the very moment I decided I would go for it, someone I didn’t even know referred me for a big double murder investigation. I was instrumental in winning acquittals on both cases, and thereafter, work flowed my way fairly consistently.
It was the leap of faith – stepping off the ledge, if you will – that was the biggest obstacle for me. It felt like something simply pushed me off that ledge, and, thankfully, my wings were working.
The biggest challenge that I’ve had to overcome as an entrepreneur was getting sued for trademark infringement by a publicly traded company within the first year of starting my business. This was obviously an incredibly challenging time, both financially and psychologically. But it also took an enormous amount of our team’s time to handle the process of defending ourselves against the suit. We had to deal with discovery requests, make decisions on motions, attend meetings, etc.
My cofounder and I decided to handle this by assigning all the lawsuit tasks to him and leaving me to run the operations. This division of labor allowed us to continue to grow the business (and fund our defense) during the twelve months we were engaged in the suit. Not only did we survive this challenging time, but when the suit was finally resolved, my business was in great shape to press forward.
