Upside Down Entrepreneurship

Transitioning from investor to operator. What changes?

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Having spent a long time in investing it was a hard transition for me to move to operating. Overnight I went from reviewing MIS’s to scrambling to build them and wondering why my numbers seem all over the place! Doing an MBA and taking a 2 year break didn’t help much either when I wanted to get initiated to the hustle and bustle of startup life.

But it has been utterly rewarding stepping into an operator’s shoes. As I reflect back on the journey I am actually grateful to my investor training as it helps me

• Think through the priorities of the company clearly – What should we be focusing on? Even more importantly what should we not be focusing on right now? The ability to sort through the noise and be 80/20 in my execution approach has helped me streamline the team’s priorities and made us more targeted with execution.
• Talk numbers – and work backwards from company level OKRs. Yes we want to increase ARR by 200K this quarter – but where will growth come from? Outbound sales? How many new customers do we need to close to hit 200K if my ACV is 10K. 20? Ok so how many demos does that translate to if I convert 10% of my demos – how many calls do I need to book those demos – and so on and so forth it goes.
• Yet sometimes the investor mindset is more hindrance than help. My first month in the job was a lot of unlearning so that I could get myself ready to learn again. It took me time to realise that As an operator – you need to think fast and execute even faster. Those perfect decks, that perfect email, the perfect workflow – are all slowing you down in getting things done. Test, fail, iterate, test again – and let a 70% solution work – be efficient and effective, not perfect.
• Poking holes in business models is easy. Plugging them is much harder – you can read all the linkedin blogs and twitter threads on how to be the best manager ever but when it comes down to getting the team to execute at their peak capabilities – you need to customize your approach for each employee. There is no one size fits all here
• Being lean is extremely critical – throwing people at the problem is rarely the solution. Learning to be a jack of all trades, giving people stretch goals which they haven’t ever performed before – is key to building in an efficient manner. As an investor you had a theoretical org structure every company would need – and then you would plug the gaps. As an operator the concept of org structure is more flexible – especially at the earliest stages. Its better to think of it as the job to be done matrix – and who on the team can pick up that task – instead of having specialized silos.

Operating effectively is quite the challenge!