Welcome to All In, where we sit down with some of the most inspiring people in the wellness industry to find out how they got their start, their successes and their struggles, and their top advice for aspiring entrepreneurs. Next up is Helena Cawley, founder of SweatStyle.
While working as a lawyer, Cawley co-founded Uplift Studios, a women-only boutique fitness studio in NYC. She then made our activewear dreams come true by launching SweatStyle, an activewear subscription service that delivers a stylist-curated box of pieces from some of the top athleisure brands, straight to your door. SweatStyle is finally expanding to Canada thanks to a partnership with Lole. Here, Cawley shares some of her top entrepreneurial wisdom.
You have launched not one, but two successful companies. Can you recall the first inspiration you had to start your own business?
I remember a turning point in my career as a lawyer where I had to make the decision as to whether or not I wanted to try to make partner army firm. I didn’t see myself staying in practice for the long run, but I had very little experience doing anything else. So if I wasn’t going to be a lawyer forever, then I realized I would either need to start in the mailroom somewhere or create my own business. The idea of starting something out of nothing was so fascinating to me. One day this company didn’t exist and the next day it did. It was thrilling.
What were some of your early entrepreneurial challenges? What are some challenges you still face today?
Being an entrepreneur means facing challenges every step of the way. There is always more that goes into launching a business than you realize at the outset. At the beginning, it was about finding the right people to bring into the company who shared my vision, passion, and willingness to do whatever it takes. I made some mistakes on that front early on.
Once you get the business off the ground and start to move into a growth period where the business is more stable, it can become a challenge to make sure everything grows at the same pace. When customer demand outpaces inventory, you have the problem of a lot of people waiting for their orders and you may not be able to deliver in time. That’s what a lot of people consider a “good problem” to have but I have found it to be one of the hardest because the last thing you want to do is disappoint your customers.
“Spend all your free time on it and sacrifice sleep and social life if you have to. Once you know it’s solid and you can support yourself from the business, then go all in.”
Were you working a full time job when you launched your business (as a side hustle) or did you go full-force into the new business? Would you recommend the approach you took?
I was fortunate to have a partner mentor at the law firm where I worked who supported my vision. He granted me a three-month leave of absence from the firm (unpaid) so that I could explore the new business full time, but still know I had a job to come back to if it didn’t workout. I realize that’s not always going to be the case, but for me it was really reassuring to know that I wasn’t going to be unemployed in a few months if things didn’t take off.
I understand the desire to go “all in” and quit your job to follow you dreams, but personally I think you’re better off making your business a side hustle for a while until you know you’ve really got something viable. Spend all your free time on it and sacrifice sleep and social life if you have to. Once you know it’s solid and you can support yourself from the business, then go all in.
You launched Uplift with two partners but founded SweatStyle solo. What have been some of the main differences between the two paths and what has been both challenging and rewarding going out on your own?
A great benefit to having business partners is of course that you have more people to divide the work. With Uplift, we each had our own areas of expertise and it worked really well to let each of us take the lead in certain things. It can become cumbersome though, if you require unanimous decisions for everything. Getting three opinions on each decision will inevitably cause delays and could become frustrating. We managed to divide and conquer really well and had a great partnership, but that’s not always the case.
One of the best things about starting a business on your own of course, is hat you get to call all the shots. But even though I’m the sole “founder” of SweatStyle, by no means did I build this on my own. I’ve always had help either through employees, partners, investors, or advisors so I have always had the support I needed. You can’t build Rome in a day and you can’t build a company all by yourself.
Did you seek outside investment with SweatStyle and if so, how did you go about that process?
I did raise two small friends and family rounds of investment at the outset, and since then I have been bootstrapping. I initially raised the money through my network of personal and professional contacts and although not raising additional money since the beginning can temper the ability to scale more quickly, to me it was more important to seek profitability early on and scale later.
Some businesses are the opposite (tech companies for example),where they seek to grow as fast as possible and worry about gross margins and cash flow later, but I couldn’t see myself running a company under those terms and so it’s been more important for me to get a break even before I scale, which we did do at the end of 2017.
“You can’t build Rome in a day and you can’t build a company all by yourself.”
Launching – and then running – your own business can be overwhelming. How do you stay focused and on track on a day to day basis? What are some of your top tips?
I have two little kids at home, so that on top of running a business is definitely overwhelming! I think ultimately though it has helped me be both a better mom and a better entrepreneur because I devote all my focus and attention on one at a time.
Early mornings are strictly for my kids, then I work hard all day and stay very focused so that I get everything done quickly and can get back to my kids before they go to bed. Then I usually get back onto my computer at night after they’re asleep. It doesn’t leave a lot of time to socialize with friends, but I do make that a priority when I need a little “me” time. I don’t waste a lot of time in my day – I really can’t afford it.
What’s the best piece of advice you’ve ever been given as it relates to running your own business?
A friend once advised me: “If you aren’t at least a little embarrassed, you’ve waited too long.” I have definitely had the moments where I wanted to make changes to my website some more or wait a little longer to launch something to make sure it is perfect, but it’s easy to tinker your way out of relevance. If you wait too long, you could risk getting beaten to market.
There will always be things you’ll want to improve and that comes with the territory of being an entrepreneur and never being satisfied with your business. But that’s not necessarily a bad thing because it keeps you motivated and focused.
What’s the best piece of advice you would give to a woman interested in starting her own wellness business?
Make sure you have something that is different and special. There’s a lot out there right now and the space is pretty crowded already, so focus on delivering a product or service that is unique.
One of the first things we learn about starting a successful business is that you have to relieve a pain point for the public. What was the problem you set out to solve with SweatStyle and how have you solved it?
Shopping for workout clothes can be really difficult because you’re forced to try on tight fitting clothes in a small dressing room with a perky, size 0 sales girl standing outside asking how your sports bra fits. It’s much more comfortable to have the option to explore these pieces in the comfort of your own home.
But buying activewear online can be really hard in terms of getting the fit and style right just from a website. We combine the comfort and ease of trying on at home with the security of knowing that the pieces you receive in the SweatStyle box are specifically chosen for your lifestyle, fit, workouts, and preferences from our team of stye experts.
We’ve come a long way from wearing our partner’s sweatpants and an old “Co-ed Naked” shirt to the gym. Why do you think we’re so much more focused on dressing well for our workouts?
A healthy lifestyle and a regular fitness routine have become much more common and widespread. More people than ever are exercising and staying fit to live a longer (and healthier) life. So you need the clothes to go along with it! And the activewear designers realized, smartly, that we’re going to want to look great in our workout clothes just like we do in the rest of our day. We care about what we wear to work, what we wear on a date, what we wear to a party – why weren’t we caring about what we wear to the gym?
Once the market started to provide more trendy and stylish options, it became immediately apparent that we do, in fact, care about it. When you have a great new workout outfit that makes you feel strong and sexy, there’s an extra kick of motivation to run that extra mile or make it to that extra spin class this week. It’s motivation in a nutshell.
Tell us a bit about the SweatStyle partnership with Lolë and how they’re helping you bring SweatStyle to Canada.
Lolë has been one of our favorite brand partners since the launch of SweatStyle. Our customers love the versatility and stylish qualities of their clothes. It seemed a natural partnership to bring an exclusive “Lolë x SweatStyle” box to Canada as a way for Lolë to reach their customers in a new and different way, and for SweatStyle to expand into the Canadian market.
The items are exclusively Lolë in these boxes, which is different from our U.S. business, but we bring the same model where a style expert will select seven pieces for you based on your personal profile and you pay only for what you choose to keep. We’ve had an amazing reaction to it so far and we’re really excited to grow this together.
SweatsStyle boxes always feature the latest trends in athleisure. What are you predicting will be the next big thing(s) in athleisure?
Activewear and athleisure are becoming a wardrobe staple and we are wearing these pieces even when we aren’t working out! I think that trend is going to continue and we’re going to see a lot more crossover items, such as dresses made out of activewear material to be relaxed and wearable. We have too much else to worry about these days than being uncomfortable in our clothing!
All images courtesy of SweatStyle