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First-Time Founder Confessions: The highs and lows of launching your first company

Founder Stories

First-Time Founder Confessions: The highs and lows of launching your first company

Words Simon Lovick

January 25th 2022 / 5 min read

Do you remember the first time you rode a bike? Before you did it, you were probably trying to recall everything you’d been taught, as well as attempting to imitate what you’d seen other people doing. But in reality, as soon as your wheels start moving, you’re learning on the spot, and essentially, making it up as you go along. 

Starting your first business is pretty similar. You can learn as much as you like about entrepreneurship from books, tutorials, or business degrees, you can even identify role models and try to emulate their successes; but in practice, most founders will tell you, you learn infinitely more by doing. 

It’s a daunting prospect, and is perhaps the main thing that deters the majority of us from founding businesses. So what is it really like being a first-time founder? We speak to five founders currently helming their first businesses, understanding the highs and lows of being a first-time founder, and asking what they wish they’d known before starting.

Shona Chalmers

Roomix, Co-founder & CEO

Previous experience: Venture Design (Founders Factory), Senior Inventor (What If Innovation)

Mark Apter

Roomix, Co-founder & CPO

Previous experience: Head of Innovation (L’Oreal), Head of Trading (Moonpig)

Matt Kennedy

Again, Founder & CEO

Previous experience: Venture Design at FF, Innovation at Pentland, Packaging at Unilever

Omar Ismail

Temple, Founder & CEO

Previous experience: Growth @ Mixcloud, VC Investor @ Supernode

Tania Kefs

Jurnee, Co-founder & CEO

Previous experience: First employee & VP of Customer Success (Aircall)

Reasons for founding your first company

The choice to found your first business is often a deliberately radical alternative from traditional, corporate careers. You’re likely passing up job security and top salaries, in exchange for taking up an opportunity where you’re far more self-oriented, self-starting, and self-reliant.

Omar Ismail, CEO and founder of Web3 membership platform Temple, found he struggled to fit the ‘good employee’ mould. “If I strongly disagreed with the overall strategy, I struggled to stay quiet and get in line.” First working in investment banking, then in a Growth role at music startup Mixcloud, Omar quickly realised he craved a role where he’d be at the top level of strategic decision making. 

The desire to create something of your own is another big motivator. Shona Chalmers, co-founder of DIY startup Roomix, had always worked in venture design roles, including being part of the Founders Factory venture design team. She’d worked on a number of projects, building ideas from scratch—and that’s how the idea of Roomix came about. 

“I’d always worked on projects, working a couple of months at a time, but I was craving something longer that I could commit myself to and really get under the skin of,” Shona says. 

For Jurnee co-founder Tania Kefs, the inspiration to start her business actually came from experiences in her prior career. She was the first employee at Aircall (the cloud-based call centre software), and had witnessed the challenges the companies face when scaling, particularly around culture and work fulfillment. This is what led her to the idea for Jurnee, which is looking to transform virtual and in-person team experiences.    

Problem solving was also at the heart of Matt Kennedy’s decision to launch his first company. Across various positions, on the FF venture design team and as a corporate innovator, he had experiences building products to solve problems for consumers. He was looking to have a bigger impact and build something transformative. 

“To truly innovate you have to change the system that you’re operating in. That’s what led me to designing businesses rather than just products,” Matt says. He’s the founder of circular economy startup Again, building cleaning infrastructure for reusable packaging.

The best advice I received?

“Focus. Don’t keep throwing out different features and a broad range of things, focus on a specific problem and specific customers. Strip back, do one thing really well, and see if that works.”

 –  Omar Ismail, Temple, founder & CEO

Being a first-time founder—the positives

The feeling of taking full ownership over something, for the first time, is a sensation which really resonates with first-time entrepreneurs. Most founders will experience this, but the work-lifestyle shift is most noticeable in the first instance. 

“It’s that feeling that ‘I am my own boss’ for the first time ever. Obviously we’re working longer and harder than ever, but there’s something liberating about knowing it’s 100% our own choice to be here,” Shona says. 

There’s also a great joy in seeing your ideas come to life. Matt has revelled in seeing Again grow from a simple idea into a business. “There’s something amazing about taking an idea from your mind, putting it into a pitch deck, validating it, building it, and turning it into something where you have customers, investors, and a team who feel passionate about something that, just six months ago, only existed in your mind.”

There’s also a sense of infinite possibilities that come with a project that really belongs to you. Omar calls this “boundless rewards”, essentially the feeling that the company you are building, if things go right, could grow into something with thousands of employees and millions of users. The work may be hard, yes, but the fruits of your labours are endless.

As with doing anything for the first time, there’s an incredibly steep learning curve. As an early-stage founder, you’re really expected to get your hands dirty and do everything. Mark Apter, co-founder of Roomix, came from commercial innovation roles at B&Q and L’Oreal: compared to previous roles, he is learning new things every day, an aspect that challenges and excites him in equal measure. To take stock of everything they’re learning, he and Shona share each of their top learnings in every Monday morning meeting.

The best advice I received?

“What you don’t do is just as important as what you do do.”

 – Matt Kennedy, Again, founder & CEO

Being a first time founder—the challenges

The experience of being a first-time founder isn’t all positive. There are a number of challenges you’ll face on the first outing, which with the benefit of experience you may have avoided. 

The feeling of taking full ownership over a startup can be both exciting and overwhelming. “The success of the business is 100% intertwined with your success as a founder and an individual,” Shona says. This can be an amazing feeling, as good days feel rewarding. But this can often leave you feeling exposed, especially when taking on feedback or accepting failures. 

‘Imposter syndrome’, something many people face during their early days in any role, is also familiar for first-time founders. “It’s that feeling that I’ve never done this before, and now I’m a CEO,” Omar says, “Am I actually doing this right?” 

A great deal of uncertainty comes from the responsibility you carry as a founder. You are the number one decision maker at your company—and in the early days of a startup, there are countless decisions to be made. With experience, founders begin to understand the nature of these decisions, as well as how to prioritise them. But for first-time founders, this confidence doesn’t come as naturally. “There’s a discomfort in a situation where you aren’t 100% sure on something, but you are 100% responsible for it,” Matt says. 

This can throw up major feelings of doubt, especially when you don’t have teams or co-founders to validate your decisions. If that doubt builds up too much, it may even prevent you from acting or taking the risks that come with launching a startup.

Matt found that building Again through the FF venture studio gave him a buffer to make calculated decisions about the company. “We had the freedom and headspace to figure out where our niche was in the industry, and where we could add exponential value,” Matt says, avoiding the temptation to commercialise too early on, and seeing the direction of the company pivot significantly. 

Loneliness is another familiar feeling for first-time founders. Compared to being a part of teams, founders have to get used to working alone a lot of the time. 

For Tania, having access to external support and advice on these decisions was one of the top benefits of joining the Founders Factory accelerator, both through the team of operational experts, but also the vast network of founders (both on the accelerator and alumni). For first-time founders, it's a huge asset having someone close to you who has recently been through the same process and can give you insider tips on the industry. There are also numerous opportunities for collaboration, and even for getting your first users. 

Omar, currently building in the Venture Studio, agrees with this—”You’re never alone. You’ve got a huge team around you: really experienced and seasoned operators, as well as more junior people who have the time to really be there for you.”

The best advice I received?

“Pick the advice that you choose to follow. Everyone tells you different advice, everyone has an opinion. But ultimately, you’re accountable for choosing, so you have to make sure you're comfortable with the decisions you make.”

 –  Tania Kefs, Jurnee, Co-founder & CEO

Valuable lessons learned

Founders will tell you that you learn new lessons every day. Here are some of the most valuable lessons our first-time founders learned:

  • You need to be adept at switching mindsets. In the space of a day, Shona says, you might have to plan a one-year budget, write a job description, and decide where to place a call-to-action button. Each decision is as important as the last, so you need to be able to apply yourself equally and thoughtfully to each. 

  • There’s value in ‘faking it til you make it’. Founders should have the confidence to “go out there and be a company from day 1”, Omar says. For Temple, Omar was keen to build a brand, a name, and a landing page even before he’d assembled a team and a clear product, as a way of building validation and getting early momentum behind the company. 

  • There’s no shortage of people who’ll offer you advice. It might feel lonely, but you’re never alone. Whether that’s the support network you get on an accelerator like Founders Factory, or even just a community of founders on LinkedIn or elsewhere, there will always be someone to advise. But, working out the best ways of using those advisors to help you is critical. This could mean 1-2-1s with your advisors separately, then a periodic advisory board meeting, all conducted on the back of solid information packs. Or could just mean reminding yourself periodically to ask your trusted advisors the hard and big questions.

  • Know when to be humble and when to be stubborn. This is a fine balance for first-time founders. “You need to have the humility to accept advice and pivot on certain aspects; but you also need to know when to stick to your guns,” Shona says. This can be hard, given the range of feedback you’ll receive. But make sure you don’t alienate your supporters—employ high EQ here to keep them onside when you disagree

  • Being a first-time founder can be advantageous. While seasoned founders may have the confidence that comes with experience, the novelty that comes for first-time founders is unrivalled. “You bring insane amounts of energy, and a fresh, contrarian perspective that experienced founders may not have,” Matt says. 

  • It’s okay to have bad days. It’s easy to be overly hard on yourself as a first-time founder. So you need to be comfortable with admitting you’ve had a bad day, taking stock of that, and learning from that experience

  • Growth and momentum is not magic. You need to work really hard at driving growth and momentum all the time; going to market early, rolling up your sleeves and filling the pipelines. It’s your responsibility, and as Simon Rogerson highlights, is mostly just about doing the graft.

The best advice I received?

“At some point you need to draw a line in the sand and just go for it. You can be at risk of circling around different options for too long.”

 –  Mark Apter, Roomix, Co-founder & CPO

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