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The other week, I had the pleasure of hosting a panel with three of our fantastic portfolio founders, discussing their journeys from startup employees (operators) to founders of VC-backed startups. As it was an off-the-record discussion, I’ve summarised some of the key themes and discussion points and tried to capture some of the quotes/moments from the evening.
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The decision to leave a stable job and pursue the risks of entrepreneurship is a big one. Many of our founding teams were leaving objectively successful organisations and in the process, walking away from a lot of potential upside. The founders shared various triggers that prompted them to take the leap, such as ideating on startups via side hustles, frustrations with previous employers or the desire for faster progress. One founder, in particular, had a "kick in the ass" moment when a prior colleague of his left to found a business and raised capital, helping trace out the path others could take.
Building validation in your idea and displaying some early execution proof will go a long way to help derisk the jump before you make the life-changing commitment. Depending on the type of business you pursue, you can make varying degrees of progress without FT commitment (enterprise product vs. smaller buyers).
Every founder's journey is long and arduous, with numerous challenging periods and setbacks. When you’ve hit three months straight of competitors announcing huge funding rounds, customers churning, or struggling to fill those engineering roles, you are carried through by the obsession to solve systemic industry challenges and, most importantly, improve the lives of your customers and end-users.
Both Miles and Elliott had previously built startups in sectors they weren’t obsessive over and stressed the importance of passion for your chosen domain. Most VC-backed startup journeys are 10+ years minimum, and if you're going to commit the best years of your life to something, it will make it a hell of a lot easier if it’s a cause or problem aligned with the founding team's natural interests.
While the journey is exciting and fast-paced, it can also be a lonely one for founders. All the founders on our panel emphasised the importance of self-awareness, understanding your weaknesses, and surrounding yourself with complementary co-founders or team members who can fill those gaps. As one founder stated, "Who you are around is incredibly important, especially when the going gets tough."
For solo founders, the sense of isolation can be even more acute, as you will be protecting the wider organisation from the realities and struggles at the top. However, the panellists encouraged founders to tap into their existing networks, noting that many resources – technical and non-technical – may already be available, especially within your existing firm, and these conversations could often lead to co-founding relationships.
The dedication and sacrifice required to build a startup as a founder are pretty high, but the same is true for early employees (with far lower equity ownership). The panel debated the different routes and levels of involvement in a startup, whether as a co-founder from the beginning, an early employee, or an operator joining at a later stage like Series A or B.
Each role presents unique challenges as well as opportunities, and you should think about where you are in your career and which type of role best suits you and your circumstances. Survivorship bias ensures you hear the stories of early tech employees making multi-generational wealth if you join the right startup at the right time; however, according to AngelList data, a venture-backed seed-stage startup has an estimated 1 in 40 shot—or 2.5% chance—of becoming a unicorn today. If you are taking that sort of risk, you should consider whether you’d rather own 1.5% or 50% of the company.
Equally, once a company has been further derisked, at Series-B+, for example, it could be seen as a more sensible trade to join for basis points of equity. Speak to people and work out what best fits your situation.
When asked about skills they wish they had or found invaluable, the founders highlighted sales abilities, technical aptitude in-house, and embracing the comfort in not knowing – the ability to navigate uncertainty, leverage the expertise of those around you, and continually learn and adapt.
The entrepreneurial journey is one of constant reskilling and learning. You are never complete as a founder, as each stage will present new challenges. The above skills were things they have reflected on to date but are by no means extensive.
As a founder, your energy and communication style set the tone for your entire team. The panellists emphasised the importance of being able to lead through example, energy, and motivation. When things aren’t always going to plan, embrace pivots by framing them as the byproduct of learning and new opportunities, maintaining honest and transparent communication to avoid surprises, and "over-communicating" to keep everyone aligned and motivated.
Securing funding is a critical milestone for most startups, but the founders cautioned that raising venture capital should not be viewed as validation alone. "As soon as you've raised money, you start the clock," one founder warned, emphasising the growth expectations and pressure that is attached to external funding.
Building relationships with investors who share your vision and align with your thesis can increase your chances of success. The founders recommended dedicating a small but consistent portion of time, around 2-5% a month, to engaging with VCs and nurturing those connections.
Finally, the audience asked some questions. One attendee was interested in how to generate excitement and a sense of urgency among investors. The founders shared strategies like leveraging "echo chambers" by concentrating fundraising efforts in batches, securing early commitments from angel investors, and carrying themselves with confidence through follow-ups and presumptive closing techniques.
As one of the panellists noted, knowing your "line in the sand"—the terms you're willing to accept or walk away from—can also be a helpful negotiation tool.
Overall, the Operator & Friends <> Concept Ventures event covered many doses of reality, including the initial leap of leaving a stable job, securing funding, and navigating the challenges of building a successful startup. It's not an easy journey, but it can be immensely rewarding for those truly passionate about their work.
A big thanks to the Operator & Friends crew for filling out the room with some great people!
If you're considering starting a company and want advice on what to expect and the journey, contact Olly at oliver@conceptventures.vc.
