When Startup Yoda Came to London

Five lessons on Mental Health and Entrepreneurship from Jerry Colonna @Reboot.io workshop in London, 9th February 2016


Ok I admit it, I was a bit like a teen schoolgirl meeting Bieber last Tuesday, but in a reeeeeeally geeky way, when I got to join forty other founders at Makers Academy, for a workshop with Jerry Colonna talking Mental Health and Entrepreneurship… the guy is a Zen master, executive coach, authenticity guru, who cut his teeth as a private equity beast at JP Morgan and then founding partner of a VC in the mid-90s, with such a gentle style balancing his gritty Brooklyn baller vibe…. and I’ve been an avid subscriber to his podcasts for, well, a long-time.

1. Invest in carefree, unfocused time

Jerry shared a really helpful way to think about state of mind and energy… basically we’re all always roaming around between these four squares. On the X axis is Negative -to- Positive emotions, Y axis is Low Energy -to- High Energy — there were two key messages.

Firstly, the more time you spend in the red zone (survival based feelings — angry, defensive, tense etc) the more likely you’ll drop into the grey zone (burnout, low energy and negative,defeated, empty, sad); on the flip-side if we want to spend most of our time in the blue zone (high & positive energy — where our greatest performance happens), we have got to respect and take care of ourselves, and ensure we invest solid chunks of time in the recovery zone (bottom right — low and positive energy — carefree, mellow, relaxed, unfocused) to recharge, reflect and prepare.

This second-piece was the most contrarian for everyone… taking a break and NOT WORKING IS GOOD FOR YOU AND FOR YOUR BUSINESS. For reals. Think long walks in the evenings, a workout session, entire weekend days properly blocked-off for unplugged R&R time — it’s all really important to support your ability to perform. And, this is the zinger, we don’t have to feel guilty when we’re chilling… Sit on that sofa and watch another episode of Narcos(!), you’re investing in your resilience. As a runner it makes a ton of sense…. you can’t keep running 10k after 10k every day, you need complete rest days, you need to feed yourself wholesome, nutritious food, you need slow jogs and then you hit your performance days. Your mind’s just another muscle. AWESOME

2. Check the vibe, check the melody

The idea of using a Red/Yellow/Green check-in with everyone before a meeting (or at least important meetings where group discussions and decisions are going to take place) totally hit home.

It’s simple, before kicking off a meet, you go around the room and everyone shares whether right “now now” (Kenyan for right now) they’re feeling Green (great, calm, rested, ready to go), Yellow (OK, but bit on edge, mind preoccupied with other things / concerns), Red (here in body only, mind is completely off piste and not in the here and now) — here’s a more detailed sketch-out on this tool.

I’m gonna try it in upcoming sessions with my bro Alex (we’re cooking up a new venture right now) and @Penda. On reflection, I remember in 2015 when things were getting very intense and high pressure at Guevara we were having cofounder/mgmt meetings re strategy, or I would run product roadmap sessions with my engineers and creatives where, on reflection, most of the people at the table were in the Red or Yellow zone and hence they were complete clusterfucks of meetings, decisions were either impossible to reach or I bludgeoned them by sheer energy, brute force and the shadow of deadlines. Just entirely pointless wastes of energy, sometimes compounding the dormant problems.

3. Promotion as a kiddie

Jerry went deep with one guy, let’s call him Ben, and amidst the quizzing and probing he surfaced a classic entrepreneur feeling, that a lot of us echoed, that Ben had to maintain an outer shell of strength, determination, certainty, belief for his cofounders, team, investors, partners etc… as everyone looked to him to be that rock. Jerry spotted this and asked to dive deep, asking about his family background etc, and identified that Ben, in his teens, had experienced something they call “Early Promotion”, where your home/family situation is such that you assume responsibility for maintaining and protecting the inner happiness of your family, before your time, this can happen in all manner of situations.

Wow, this one resonated big time for me. Brought rushing to mind my teen experience helping my ma battle depression. As the eldest, and with a pa who dealt with it by largely not engaging in it, I totally felt responsible and, with no idea what I was doing, tried all I could to help my ma in coping and recovery, and to protect the happiness of Gemma and Al who were younger then. Found it really interesting (and actually somehow reassuring to hear!) that this experience of “early promotion” is something Jerry and Ali find that entrepreneurs are way over-indexed on from their past, which gives rise to wanting to be a leader and take care of everyone.

4. Just being heard

We hit up an exercise, in which we did a 30 mins walk with somebody we’d never met before with a single objective, for each to talk about our greatest struggle for 15 mins each, and then come back and share the other’s story with the group…. Jerry highlighted how powerful the opportunity to “listen, truly listen, compassionately, and not try to fix or judge, just listen and let the other person feel heard” … and likewise how good it was to just be heard by another human being…. and be allowed to be your whole true self.

I took off with my new compatriot, Rich, and had an epic, incredibly candid conversation, while meandering around the back streets off Brick Lane. I felt a really stark reminder of just how amazingly lucky I was in the first two years of building my first startup… I just happened to open our office across the corridor from Amon (who was doing the VC thing at Acumen Fund, and became a very special friend) as well as, having my office front-door inches from the front-door of Nick (who was building Toughstuff, and is now my cofounder @Penda). What a blessing. What this meant was that we grabbed lunch at least once a week for 1–1 catch-ups about how work was going… mentoring, supporting and just being there to listen to each other. Not to mention the dozens of other great friends who were also founders in Nairobi, rolling the dice, building a vision, feeling the uncertainty and riding the rollercoaster.

This really was such a luxury, an empowering, incredible luxury. Particularly in the second year as shit got really really tough with our stuttering fundraising, the long-drawn out partnership deal with Safaricom and Commercial Bank of Africa, the wranglings with the Central Bank, and then eventually my (remote in UK and US) cofounders (completely fucking me).. if I hadn’t had those guys, Nick and Amon, right there, in the building… so that I could pop my head in after a complete meltdown and just say “hey, can we go grab a mango juice / chapo / mandazi?”. I was in pieces anyway, I dread to think. Genuinely amazing. So lucky. I am so grateful.

5. “Be more JP”

I spoke up and mentioned that when walking and talking with Rich, it was an unfamiliar and great feeling exactly because I was talking to a stranger, who carried no preconceptions of me and to whom I don’t need to be anybody or maintain any facades or pretences… which crazily when I think about it, with all of my loved ones — family, other half, friends, cofounders, colleagues — I feel an implicit expectation that governs my behaviour in interactions with them, it might be strength or happiness or certainty or stability — but the context creates a filter through which we act.

Knowing I wasn’t being judged, and with the brief to “talk about our greatest struggle that nobody else understands” I felt completely unfettered to BE MYSELF and expose what I really feel and fear. Things that I barely ever think about, but kinda knew were there, came out… and turns out that feels damn good as I was allowing myself to BE MY TRUE SELF. Jerry, kept embarrassingly referring back “See? We all need to try and be more JP”… really hammering it home (mild cringe — but of course my ego somewhat loved being called out — over and over). But, more importantly this emphasises to me the absolute utter importance of finding ways to continuously connect with and express our true inner authentic self.

Reboot’s stated raison d’etre is to “help people achieve true authenticity and self-actualisation through radical self-inquiry”, Jerry emphasised to us: “you didn’t go through all that slog of launching your startup to live a life on someone else’s terms…”. This really reminds me of the way that my brother Alex thinks about his approach to starting something, it’s important to ensure that you’re creating the rails for self-actualisation by doing those things that are truly authentic to who you are, that means thinking deeply about where YOU are coming from and where YOU want to go… do the hard thinking, then do the hard work to make that so.

Jerry synthesised this all with a killer quote “a life lived like a mobius strip is a life fully lived”. When you are able to be, with no difference between what’s on the Inside and what’s on the Outside, that’s our pursuit. You make them one and the same. It’s so hard… but it feels SO DAMN GOOD when you do it.

But what about in the real world?

Perhaps unsurprisingly, most in the room at this stage, were now thinking, OK how do I bring this back to the daily-grind of my business(?), is it really possible to survive without pulling each persona I need everyday to win the games of managing staff, investors, journalists, friends, family etc. My buddy Dan put it straight at Jerry “Twenty years ago, if a founder came in to pitch you being all authentic at Flat Iron Ventures, would you have backed his startup or laughed him out of the room?”

Turns out Jerry’s hit this for a home run before… His response was “You have to bring your authentic self, bring your wounds into your business”, don’t ever deny who you are. He illuminated this with the story from his beaut podcast where, during a live session with an entrepreneur, they uncovered that she had experienced intense bullying at school at the age of 13, and ate lunch alone everyday in the toilet cubicle to avoid the bullies, for a year… and now she’s building a startup that encourages teams to come together everyday for lunch through food to build community in the workplace (?! I know it! You gotta listen to this one — Reboot.io Podcast #28 Reclaiming the Shadow). Crazy thing is she really had not realised she was building this startup for her 13 year old self, Jerry encouraged her to weave this story into her investor pitch and, although many would think that this type of soppy story wouldn’t stand-up in the heat of a VC partners pitch, doing so unlocked a crazy round, boosted her whole company’s culture and has erupted their growth. Correlated?

So that’s what I heard and experienced at Reboot.io does London… some epic tools, and powerful reminders of how damn good it is to be heard, really heard and just be you.


p.s. gotta shout out the way Jerry opened by introducing Ali Schultz with “if it wasn’t for my cofounder I’d still be sitting around saying, wouldn’t it be great if . . .”. That’s such a simple and clear honour to share about your partners-in-crime, and so how I feel about the best cofounders I’ve ever had, Nick and Steph @PendaHealth, and what I would love to have the honour to say about future collaborators too.

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