How to scale your ‘Founder Mode’
This piece was first published here in Sifted
Y Combinator cofounder Paul Graham recently released a blog post called Founder Mode, which set Silicon Valley alight. In it, he referenced a talk Brian Chesky (of Airbnb fame) gave at a recent YC event, where Brian’s message was that conventional wisdom about how to run larger companies — especially founder-led companies — is wrong.
I first heard Brian Chesky make this point in Lenny’s Podcast in November last year and immediately sent the episode to my cofounder Saasha accompanied with lots of celebratory emojis. At last! Someone highly respected in the world of startups was speaking a truth that we already knew — but hardly dared say out loud. The core thrust of Brian’s message is that as companies scale they invariably bring in seasoned leaders, who the founders then need to ‘empower’ and avoid ‘micromanaging’ at all costs. More often than not, he says, the results are “disastrous” as those seasoned executives operate in “manager mode” and so “drive the company into the ground”.
The notion of “Founder Mode” and “Manager Mode” being two very different things resonates enormously because this is something we’ve experienced at Olio. We now talk about our company history in three chapters: Olio 1.0 which was when we were a scrappy under-resourced startup — firmly in Founder Mode; Olio 2.0 was all about scaling, and during that time we brought in the pros, switched on Manager Mode, burned a lot of cash and didn’t see the results we’d hoped for (admittedly not helped by the 2022–23 economic crash). And now, as of 2024, we’re firmly in Olio 3.0 — back in Founder Mode, but a more grown-up version of it.
While Brian and Paul have given founders a long overdue licence to push back on external pressures to convert to Manager Mode when the scaling starts, they haven’t given much detail about how Founder Mode needs to evolve as your company scales — and it’s crucial it does evolve, because staying in early-stage Founder Mode when your company is scaling can be just as destructive, if not more destructive, than transitioning to Manager Mode.
So, in the spirit of sharing, here are some of the tools we’ve used to scale up our Founder Mode in Olio 3.0:
1/ Cofounder brain dumps
During Olio 1.0 Saasha and I were in every meeting, driving every project. As the company starts to scale, however, that becomes completely unsustainable. Between being in the weeds (which isn’t scalable), and delegating entirely (which also doesn’t work), we’ve found an invaluable tool that helps us reach the right balance, and that’s what we call the “cofounder brain dump”.
At the start of any major project, we’ll write a document where we share our vision, objectives, hypotheses and biases (best for everyone if we’re upfront about these rather than pretend they don’t exist!) for that particular piece of work. This has proved crucial in enabling us to not only set the direction for the project, but also have our point of view firmly conveyed up front, while allowing the team plenty of freedom to run with the project on a day-to-day basis, and to challenge with data anything we may have said up front.
2/ 4Ps
There’s not much need for weekly progress reports when the company is small, because you’re all over the details already. However, as the organisation scales, you need an efficient way to get a panopticon view of what’s going on. Therefore in Olio 3.0, each week everyone (apart from the engineers) emails their line manager their 4Ps in a Google Doc.
The first P is the ‘Pulse’ section where you rate on a scale of 1 to 5 your ‘stress level’ and your ‘enjoyment level’, accompanied with a line or two of commentary about each. This commentary regularly touches on home life as well as work life, giving a really well-rounded view of how that person is feeling holistically, which makes you much better equipped to support them. Next are the three update sections: Progress made last week, Plans for this week, and Problems that need solving, ideally with some options for solutions.
All line managers also need to include links to their direct reports 4Ps, so as cofounders — if we want to — we have quick access to everybody’s 4Ps enabling us to go from 10k feet to 10 inches in just a few clicks.
3/ Skip levels, shadowing and AMAs
In the early days you know every team member, every team dynamic and which systems and processes are working or not. But as the organisation scales it can be far too easy for everyone to start “upward managing” you, making it tough to get a read on what’s actually happening.
Saasha and I have 15–30 minute monthly skip-level meetings with each of the direct reports of our direct reports. These are an invaluable way to spot problems before they occur, to instil the ‘Founder Mode’ deep into the organisation, to nurture top talent and to build strong personal relationships throughout the company.
In addition to skip levels, we’ve found that ad hoc shadowing of teams can bring to life the warts and all of their day-to-day experience, and help identify opportunities for efficiencies and cross-team collaboration.
Finally, Founder AMAs (ask me anything) at a team level have proven a really helpful way to build a more direct and personal relationship with team members who you wouldn’t ordinarily interact with, and the depth and breadth of the questions never fail to blow me away.
4/ Company all-hands
Almost every meeting is a company meeting in the early days! However, as you start to scale that quickly becomes untenable.
Each week we have a company call that everyone dials on for (cameras off apart from the first Monday of the month so people can walk, work-out or even lie down as they listen in). It starts with one to three presentations of max five minutes each, where individuals can showcase some great work that they or their team have done, or perhaps upskill the broader company on how their function works. There is then the updates section which includes a cofounder update (verbal, where we each share three things that are top of mind for us that week) followed by updates from the core business units, and updates on our KPIs. Finally, the meeting closes out with the announcements section which celebrates wins and thanks, highlights challenges and learnings and ensures that important company-wide announcements are heard by everyone.
Founder mode philosophies
Just as important as the tools you need for your scaled-up Founder Mode, are the accompanying philosophies with which you run the company. We’ve outlined these in an Olio 3.0 Operating Manual, and some of our philosophies are:
- The importance of velocity (“speed in the right direction”), coupled with agility (the ability to quickly change direction in the light of new information)
- Having the mindset of “What can we build (to solve this problem) with what we’ve already got?”
- 80% done is better than 100% perfect, so SHIP!
- The need to “divide and conquer” rather than “travel as a pack”
- The discipline of “first principles thinking” always
- And guidance on when and how to use data, user research and testing — because sometimes gut and intuition are just as powerful as these
It’s very easy as a founder to be insecure about all the things you’re not — and feel pressured to step aside for the Manager Mode pros when it comes to scaling. However, if you combine humility with ambition, and work hard on levelling up your Founder Mode, there’s no reason why you can’t ride with your business all the way to the top.
