From Heart to Hustle: The Reality of Building a Business with Your Best Friend For many, the idea of running a business with your best friend sounds like the ultimate dream. Who wouldn't want to swap office politics for brainstorming sessions over coffee, or the dreaded 9-5 grind for the flexibility to work on your own terms?
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The freedom and the sacrifice
For Demi Smith and Tiger-Lily Beck, co-founders of Flex and The City, a London based media, marketing, and events platform - a community hub for the flex world - the reality of entrepreneurship is far more complex - and infinitely more rewarding - than the glossy social media highlight reels suggest.
"You have the ability to work anywhere, which gives you a lot of freedom," says Beck, reflecting on one of the unexpected perks of starting Flex and The City, a company that champions remote and flexible work opportunities. "In the sector we're in and with the people we work with, that gives us the ability to work all over the country."
But freedom comes with sacrifice. Smith, who left a stable job to launch the business, admits that the entrepreneurial journey is not without its challenges. "You have to sacrifice a lot of time. There's a lot of hard work, and that means you may miss out on some things in your personal life," she says. "You also have to make a financial sacrifice as well. We left jobs that paid us regularly every month, and losing that regular income is a step into the unknown when you start a business."
The pair's candid reflections reveal that while entrepreneurship offers freedom, it demands resilience and a willingness to embrace uncertainty. For those considering the leap into business ownership, Beck believes patience is a crucial trait. "You have to be patient. Not everything happens when you want it to, or things get delayed, so being patient is key," she explains.
Smith agrees but adds that patience alone isn't enough. "You also need to be dedicated. There's no point working hard towards something if you lose interest when it doesn't go exactly as planned. You also need to be resilient when things get tough," she says.
Passion, too, plays a vital role in their success. "Being passionate about your subject area is really important," Beck adds. "That can help when things get challenging."
Connection is everything
Beyond personal traits, the ability to build meaningful relationships has been a game-changer for Flex and The City. "Relationships can be the difference between your business succeeding and not," Smith says. "Learning how to do that effectively has been a huge help for us." Starting a business means stepping into a world of uncertainty - something that Demi and Tiger-Lily have experienced firsthand. "Sometimes with tears!" Smith admits with a laugh when asked how they cope with the risks involved. But she quickly shifts to a more serious note. "Having a long-term goal is so important. It helps keep you focused on the end game and can be the drive you need to keep going."
The duo also credits their partnership for helping them navigate the rough patches. "It's really great that we have each other as co-founders," Beck says. "We're not alone, and having each other during those difficult periods is so helpful." One of the biggest misconceptions about entrepreneurship, the pair explains, is the idea that business owners have unlimited flexibility. Beck notes that while there's a lot of freedom, "you do lose a lot of the work-life balance a 9-5 job gives you. You always have to be available at a moment's notice as your business is your baby." Smith adds, "Everything feels personal. Any rejection or something not going exactly to plan can feel like a personal slight, but you have to try and look beyond that."
For many, financial insecurity is another overlooked challenge. "I don't think people really understand the risks to financial security running a business can have," Beck says. "Losing that monthly paycheck is a huge risk that can be daunting, especially when you are starting out."
Social media often paints a glamorous picture of entrepreneurship, but both co-founders are quick to dispel that myth. "People think entrepreneurs have everything planned in advance, but you have to be flexible and constantly adapting to change," Smith says. "You don't need to have everything planned."
Beck chimes in, "You also need to be prepared that you're going to have to wear 10 different hats. You need to be an accountant one moment, copywriter the next, COO the next, and that can be tough when you're starting. It can also mean you're working long hours — it's not all glamorous!"
The strength of a strong partnership
Running a business with a best friend can be tricky, but for Smith and Beck, it's been their greatest strength. "People say either it must be so easy or it must be really hard starting a business with your best friend, and in all honesty, I wouldn't go into business with any friend," Smith says. "But we have a sisterly bond. We lean on each other for different things and play to each other's strengths."
Their complementary personalities have proven essential. "What works for us is having the balance between us," Beck explains. "If one of us is less patient or less confident, the other will be able to step in and bridge that gap. Having someone the opposite of you helps."
Smith adds, "We also know each other so well we can leave some bits unspoken, but we're not scared to call each other out if needed. We are good at leaning on each other's different strengths, and I think that's why we work so well together, but it's not something you can do with every friend."
When asked what advice they would give to aspiring entrepreneurs, both Smith and Beck agree on one thing: be prepared for the unexpected.
"Don't be afraid to take risks," says Smith. "But also be prepared for the emotional journey it takes you on. It's not just about the business side of things — it's about personal growth too."
Beck offers a final piece of advice: "Find someone who complements you and can support you through the highs and lows. Having that support system has been crucial for us."
Their journey with Flex and The City highlights that entrepreneurship is far from a straight path, but with resilience, passion, and the right partner, it can be an incredibly fulfilling one. It is a powerful reminder that building a business, especially with a best friend, is both an exhilarating and challenging journey. The flexibility and freedom that entrepreneurship offers are tempered by the sacrifices, long hours, and constant need for adaptation. Their willingness to embrace these challenges, however, has led them to growth, both professionally and personally.
For aspiring entrepreneurs, the key takeaway from their experience is the importance of patience, resilience, and strong relationships. As they navigate the ups and downs of business ownership, their partnership remains their greatest asset. Their complementary strengths and shared commitment to the mission of Flex and The City have helped them not only survive but thrive in a competitive industry.
Ultimately, their story illustrates that entrepreneurship is not a glamorous pursuit but a deeply rewarding one when approached with authenticity, dedication, and a sense of purpose. As they continue to build their business, Smith and Beck serve as a testament to the power of teamwork, passion, and the pursuit of meaningful change in both the business world and their personal lives.