Starting a business? Valuable advice from those in the know

Starting a business and being your own boss is a dream many of us have. If you need a little nudge to help you make that dream a reality, those who’ve already done it can be a good source of inspiration. 

In Season 2 of the award-winning Hiscox Side Hustle to Small Business podcast, guests are asked what advice they’d give someone who is just starting out on their journey. Their advice runs the gamut from general to very specific, but it’s all useful if you’re looking to get a business off the ground. 

Here’s what they had to say. 

Don’t sit down

Elle Overholt, career strategist and founder of Forth LLC, admitted her advice was unusual. “This is going to be an unpopular opinion, but I’m just going to say it. The worst thing you can do is sit down.

“What I find is that people just sit and imagine and rethink and rethink and rethink, but you’ve never taken one step forward. I’m not saying quit your job and go do the thing. I mean keeping your job, (but) sitting down with one potential client. And mock doing whatever it is, creating a prototype or talking to a manufacturer that could create your prototype. 

“It doesn’t have to be doing this big thing, but taking one step of action. The worst thing you can do is not taking action. The best thing you can do is do the next best thing. Just pick one thing that could move you forward.”

Do what you love, and don’t forget about the ‘business’ side

Kat Carney of Swell & Stone is a photographer who specializes in shooting weddings and elopements in exotic locations. Her advice to would-be entrepreneurs has to do with the ‘business’ side of being a business owner. 

“Wanting to work for yourself is one (thing), right? There are a lot of things that come with being a photographer that have nothing to do with photography. So you have to be interested in all of those things as well. You have to be interested in working for yourself and running your own business. I would say honestly (that) is like 75% of it, and the other 25% is actually taking the photos and all that kind of stuff.”

Related: Thinking of turning your side hustle into a small business? Here’s how it’s done

Kat recommends finding something you know you’ll be happy doing. 

“Find something, a niche, that is really true to you. That might be different than shooting elopements in the outdoors. It might be shooting elopements in the city, or it might be shooting product placed somewhere or something like that. If you hate working with people, strive for a job that works with inanimate objects. Just make sure that it’s true to you and to the things you like doing because if you don’t love doing it, you won’t continue to want to do it every single day. And it’s a lot of work.” 

Define your mission and know what success looks like

Sean Furey was an Olympic javelin thrower, competing for Team USA in 2012 and 2016. When he retired from competition, he founded Furey Athletics, a coaching and online training resource, as a side hustle. He recommends taking small steps forward. 

“My advice would be if you're not going to just jump in and go all in, that you can find small ways to experiment and to make steps forward. That probably starts with getting a very clearly defined set of principles and a mission of, what do you want to do? Why do you want to do this? What is the service that you want to provide? And every day take little steps moving forward to getting closer to having a company or some concepts that fulfill that.”

Sean also recommends you think about what success looks like for you. 

“(For me),  this has been evolving and getting more defined as the years go on. Success is going to be when I can support myself and can support my family through education of others surrounding the topics that I love so much, dealing with sports and fitness. 

“I want to be giving services to athletes who are interested in achieving goals, This isn't just javelin throwers, but any overhand throwing, any power athlete, and maybe it will expand over time. But if I can provide services to those athletes, help them achieve their goals, avoid some of the problems that I experienced, and get higher than the level that I experienced, and support my family while doing that, that's a success. 

“I think that's really the dream. I loved throwing the javelin. I loved pursuing the Olympic Games and I want to continue, maybe not as an athlete but as a coach, learning more and more about that, and really understanding what is the best way and how can you help people achieve goals like that.”

It’s better to try and fail than not to try at all 

Mary Nakaya and Melissa Porras started Nomad Artisan Company to sell their ceramic jewelry online and through retail stores. 

Melissa says, “Even with jewelry, if we were to say, ‘Oh, there’s already earrings out there,’ we would never have done it. It’s so important for us just to get out of our own way. You will never know if you don’t start. And there’s always that ‘what if?’ in the back of your mind. So, it’s better to try and fail, whatever you think that failure might be, than to not try at all. Because if you don’t try, you’re never going to get there either way.  Why not go for your dream? If you don’t go for it, it’s just going to stay. But it’s never going to come true.” 

Mary observes that the path to entrepreneurship isn’t always smooth. “Like the road to success, you’re going to have bumps and hiccups – just start. I used to tell my high school students: Who was the greatest baseball player of all time? It was Babe Ruth. But who was the greatest strikeout king of all time? It was Babe Ruth. Michael Jordan didn’t always make his three-point shots. Success is getting in the chair and doing what you love.”

Mary also suggests that entrepreneurs shouldn’t be put off by others in the market. 

“There’s always room in the market for another artist or craftsman, or a businessman and another business. Because you have your own voice, and it’s important for the world to hear that. And maybe it doesn’t go how you want it to go, but you’re learning, you’re growing, you’re on that pathway. Be true to who you are as a creative and an individual.” 

Related: Secrets to success: Encore entrepreneurs talk about confidence

Think about where you are in life, and hire carefully

Derrick Knudsen was working at a Fortune 500 recruiting firm when he realized that recruiting firms were avoiding taking on cannabis companies as clients. Seeing a need that he could fill, he founded Meta Talent Group, which helps fill roles at cannabis, hemp, and psychedelic-focused companies. 

Derrick recommends considering your decision to start your own business carefully, and understand that there’s a lot more involved than just doing the work. 

“Something that they definitely should do is think about it for quite some time. It's not easy, you know that, I know that. You're doing everything, right? And so when you're expected to keep your inbox clean on top of sending out paychecks and invoices, and collecting, and doing the day-to-day recruitment of a position. 

“When you're first starting out, if it is a side hustle to a business and you're really shoe-stringing it, it's going to be a struggle. it's a bit of a roller coaster. You're going to have great days and you're going to have not-so-great days.”

Derrick suggests keeping in mind your current life stage. 

“I think a lot of it is just understanding where you are in your life. Who depends on you? For me, just being a single person, I feel like that made it easier, not having a family. There are a lot of ups and downs, (so) just know your footing, your foundation, and why you want to do it.” 

Derrick started his business with his brother, but once he needed to hire, he was very careful. He advises other new business owners to do the same. 

“When you're starting a business, your first one or two hires are just so important. The cost of a bad hire is already two and a half to three times the salary.

“But when you're starting a two-person company and you're making hires three and four. You almost need those to be successful, and so really taking your time and vetting out your first couple of hires  is super critical.”

Related: 4 Ways to hire top talent – even now

For more advice from small business owners who’ve done it all, subscribe to the Hiscox Side Hustle to Small Business podcast on Apple Podcasts, Google Podcasts, Spotify, or wherever you get your podcasts. 

And if you started your business as a side hustle while working full-time at another job, we want to hear about it. Tell us your story and we may feature you on a future podcast.