The Founder Rollercoaster: Fun If You Like Fear
Founding a startup is like scheduling, never as smooth as you hope.
A four-hour flight with no Wi-Fi is the perfect time to reflect on the last few months - and to write about what founder life actually feels like.
(It’s also a decent cure for plane boredom.)
TL;DR (if you want to save 3-min read time): Some days I can’t imagine doing anything else. Other days I wonder what I’m doing.
As I read this back before hitting publish, the rollercoaster post title really is the best way to describe it: you’re meant to enjoy it, but half the time you’re in fear for dear life.
But like any theme park ride, it goes up and down - so let’s take a deeper look.
Of course we start with the lows because we’re all human and like to dwell there…
The downs
Sleep + mental presence
I was chatting with another founder who said, “I hope you’re not doing the classic 12-hour founder day.” I actually don’t know how you can’t do it.
There’s zero pride in saying that, it’s just fact. I, honestly, don’t think it’s possible to avoid if you want to succeed.
The only (slightly unhinged) silver lining: I recently upgraded from Apple Watch 10 to Ultra 3 and my deep sleep scores improved - probably more about new sensors than my actual rest. Psychologically though, I’ll take the win.
The harder part is the constant mental load: replaying strategy, features, pricing, positioning. It means you’re often in your head when you should be in your life.
I’ll sit next to my wife in silence, breaking down problems in my mind, without realising I’ve gone into vegetive mode (a gear down from ‘founder mode’).
Everything costs money
The more you build, the more the cost of business and SaaS subscriptions get you in a stranglehold.
Pricing paths are genius traps.
HubSpot deserves special mention: they give you just enough to get hooked, then hit you with charges: more than 1000+ contacts ($), pay to standardise your email templates ($$), see who visited your site ($$$), etc.
Balancing spend to fuel growth now, while keeping retention and sustainability in mind, is an art form I’m still learning.
Customer feedback does’t grow on trees
Founder wisdom: “Talk to customers all the time.”
Reality: Everyone’s busy. Customer feedback is hard to get: you really need to go out and get it.
Every snippet of feedback is gold-dust. People who report bugs are diamonds. The ones who jump on a 30-minute call? Otherworldly, precious, rare.
If you’ve never founded, imagine the chef walking out mid-meal and asking for a detailed critique - it’s weird, but invaluable - and not for everyone.
Momentum needs fuel
When momentum comes, you feel like you can’t stop feeding it. We’ve been lucky in our own miniature way so far - users, Google backing, angels, advisors, VCs.
But every day I worry we’re not doing enough to sustain it. And we’re only at the very beginning, the hard work is still ahead.
Momentum is addictive, but also terrifying.
Talking to investors feels Like Tinder
We’re only just dipping into VC conversations as we prepare for our next phase. It’s a dance: hot and heavy, then ghosting, then coming back.
Sometimes it feels like they want your customer insights more than they want to invest. Over time, you build a mini-radar for what’s real vs. noise - but that’s a founder muscle you don’t have at the start.
I do, however, feel the odds are in my favour here. It took me four years to get my wife to go on a date with me, so I’m ready to play this game.
The ups
Evolution is good
We launched Meet-Ting at the end of July. Two months in, we’ve gone from closed beta to open beta, from email-only to WhatsApp, and we’ve started talking to enterprise customers.
Our mission hasn’t changed: use AI to turn messy scheduling into booked meetings.
Right now our story resonates because it combines:
Mission fountain: human connection.
Tech advantage: multiplayer AI (you + guests, not just you-to-AI).
Customer value: recruiters, consultants, founders, VCs, freelancers - the lifeline of their business is meetings.
We only got to this place by putting stuff out into the world and seeing what comes back. Until you actually say something to a customer or post in a community where they may be, it’s all just theoretical. Get out there and talk about your product, look out for body language or social engagement signals from day -1.
In my past articles for how Reddit really helped pre-product.
You get what you put in
At a startup, your fingerprints are everywhere. Every user breakthrough or team win feels huge.
I ran large teams at adidas and TikTok and loved it (still miss my teams). But here, with a small crew, every single thing is us.
And that feels different.
You do it your way
At Meet-Ting I can finally do things I always wanted:
Publish our data openly.
Write Privacy + Terms in plain English (maybe it’s the communicator in me, but I feel like it’s nice to know what you consent to in life huh?).
Make SaaS less boring (because boring booking tools = boring meetings).
Play with pricing models with fresh eyes and no cognitive baggage (e.g. I’ll never be OK with the SaaS-pattern of charging users for customer support).
Hire and curate the people around me.
The freedom is addictive.
New community
The founder community is awesome.
A bunch of people on the same rollercoaster, trying to solve problems and make life better for customers.
A special shout out to Product Hunt, I love being there. So many smart people, brought together by building.
Supportive, diverse, innovative. It’s one of the unexpected joys.
Somewhere in the middle
Luck
I used to binge How I Built This with Guy Raz, and the one thing every founder said stuck with me: luck plays a massive role.
Case in point: last Friday, a really promising partnership fell through because we didn’t want to take the direction they pushed on us.
Then Monday night, out of nowhere, one of the biggest tech companies in the world dropped us a speculative email asking to pilot next week.
No clue how they even landed on our site. Luck? Marketing? Both, probably.
Sometimes you’ve got the right idea at the wrong time. Sometimes you’re building just as a platform decides to commoditise your feature.
You can work as hard as you want, but timing, platforms, markets…
That’s the ride. One day you’re down. Next day, back up.
Final thoughts
Right now, if someone asked me whether to do it, my honest answer would be: hard yes - and quietly mouthing, no.
That’s it.
If you’re thinking about your own journey, DM me.
Thanks for being here,
-Dan
Chief Ting
Onwards!
I've never found building a SASS product especially scary... Curious how https://meet-ting.com/ is going- how many customer you got?