I was living the SaaS dream. Here's why I left

Shai Schechter • 2024

RightMessage has been a wild ride.

What started in 2017 as a passing conversation with a guy from the internet turned into a career pivot and a $75k-revenue SaaS launch and a $700k investment and a 10-person team and an almost bankruptcy and a rebirth and millions in revenue and…

I’m getting ahead of myself.

The story of that 6 year roller coaster is for another day.

Today I want to talk about why and how I stepped off the roller coaster.

Why I stepped out

The last year or two of RightMessage were more monorail than roller coaster. We’d survived the wild ride, vomited and regrouped. My cofounder Brennan and I had scaled the team down, and we were profitable.

Everything was… fine.

And you know what? There was a time when fine was an absolute godsend. When I was going through a tough divorce, and Brennan was having a baby and moving to a new country, a business that brought in good money when we’d only touch it for an hour here and there was a true blessing.

But eventually we had the headspace to work on it more, and fine became frustrating. Even though we had customers, we never truly found product-market fit. Churn was always higher than we would’ve liked. MRR got pretty high, but it was always plateaued at that level.

We never found lasting, reliable growth… and the surest sign of aliveness is growth.

We’d try a new marketing strategy, or a mini pivot. Nothing would change. We’d get tired of it, stop putting as much effort in. MRR might drop a little, but barely. After a while we’d reengage and try something else. Still no growth. It was a grind.

The money was coming in, but I felt unfulfilled.1

I had this deep intuition that there are more fulfilling and impactful things in my future, and they won’t show up until I’m prepared to let go of the current thing.

That realisation didn’t even feel new when I first became aware of it. I’d been burying it for a while, not ready to look at that aspect of my life yet because the status quo felt comfortable and safe and I wasn’t brave enough to rock the boat yet.2

Once I did, it felt so true that there was no doubt it was the right decision.

Just explaining my realisation to a close friend (vs my old pattern of defaulting to saying all was good) felt like a weight lifted off my shoulders.

I sat down with Brennan to talk it over. He was relieved—he’d been feeling a similar way.

So, what are we going to do?

We talked about changing things up again. Another pivot. Reinvigorate the product, finally get it growing.

But we’d been here too many times before. “Let’s just try one more thing” was looking a lot like a while (true) loop without a break statement.

Maybe RightMessage was more Ferris wheel than monorail… and we’d been round enough times.

We used one of my favourite decision-making methods: put every possible option on the table, even if they don’t seem to make sense. Then narrow down.

Sell the company.

Let it keep running without our active involvement.

Shut it down.

I buy Brennan out.

Brennan buys me out.


We reached out to a close friend/mentor/investor too to see if we’d missed anything or if he had more wisdom to share. It was helpful to get another pair of eyes from the outside.

Selling the company seemed like a good option, but the lack of solid growth and the way the investments were structured meant no-one would’ve benefited much.

Letting it keep running didn’t solve the main issue. We’d still be responsible for it and would still feel it weighing us down. Customers would suffer. And it would dwindle eventually anyway, prolonging the pain.

But we were intrigued by the option of Brennan buying out my shares. I’d be free from the work that wasn’t fulfilling me. And even though Brennan had also been frustrated with how things were going, he could see a path to integrating it more deeply into his other business in a way that hadn’t made sense when it was a shared company. He became excited to take on the challenge of growing it in a new direction that way.

Structuring the buyout

Once we’d decided what to do the whole process was refreshingly smooth.3

First we emailed a contact at Quiet Light, a business broker, to get a rough valuation for the company.

5th April 2023, he replied with a valuation range and how he’d reached it. And he recommended how to convert that valuation into a buyout price: just apply a discount for lack of broker fees and again for it being a full cash buyout, then multiply that by my equity share.

It was an amount that I was happy to receive and that Brennan was happy to pay, which is what made the process so quick. Not never-work-again money, but definitely don’t-have-to-work-for-some-time money.

6th April 2023, Brennan and I had a short (9 message!) WhatsApp conversation where we negotiated all the terms: the specific amount within that valuation range, how much would be upfront vs instalments, and other bits like currency and what the handover process would look like. We emailed it to the company lawyer to draw up the paperwork.

20th April 2023, some back and forth with the company lawyer to clarify the terms.

21st April 2023, a final call with the company lawyer, and he sent us a draft of the paperwork.

24th April 2023, I sent the paperwork to my personal lawyer to double check.

25th April 2023, she gave me the thumbs up to sign.

26th April 2023, paperwork signed and money transferred. I’m out!

How it felt

Honestly, at first, not much different.

It was a similar feeling to the one I get on birthdays. Intellectually I know it’s a big event… at the same time it doesn’t feel like anything has changed. I’m still the same person as before.

It was strange to think that RightMessage wasn’t an active part of my life any more.

And later the more existential doubts started to show up. Worries like “I should be doing something productive with my day”. “Even though I’ve just received a big payout aaaaargh I don’t have an income any more”. Navigating feeling “purposeless” and uncertain about the future.

Luckily I’d done enough introspective work that I could recognise these as narratives, get curious about them, question where they came from and whether they were serving me (more below).

Stepping away also made it easier to reflect on what we’d actually built. Even with its ups and downs it’s incredible what we were able to create out of nothing and how many people we were able to help. I’m so proud of it all. Brennan is smart, and fearless, and I learnt so much from him. I’m a different person than I was when we started. The whole experience really shaped me and taught me about myself, how to be of service to others, and what does and doesn’t fulfil me on a deep level.

But the most profound thing I noticed in the early days was how comfortable I felt with the decision.

How certain I was that I’d done the right thing.

Someone asked me whether I’d regret leaving if in future the company got mega valuable. I honestly wouldn’t. There was no doubt in my mind that this was the right thing to do at this stage of my journey. I stood tall and acted on my intuition. That’s all we can ever do. If the company gets big now, that’s how the journey’s meant to play out, and I’m all for it.

What next?

The one thing I knew was I didn’t want to dive straight back into work.

Our society loves productivity for its own sake. We praise never-ending ambition. We often don’t stop to question whether we’re even enjoying the ride, or how much is enough.

A person can miss their whole life that way.

We’ve come to accept that adults are stressed because they work so much. But what if it’s the other way round: we work so much because we’re stressed. Work is distraction from ourselves.

I want to become truly comfortable with being, before I layer doing back in.

More generally we think the world around us affects what we feel and think. But I’m realising that that’s the other way round too: everything we encounter is a reflection of our inner world.

I want to use this time and space to uncover more about myself.

To question the things my mind tells me.

To see what old narratives are still playing. Thought patterns that are trying to keep me safe but are ultimately holding me back.

That’s the best way I can have a positive impact on myself, the people around me, and the wider world. And since a business is a reflection of its founder(s), it’s also the most valuable thing I can do for whatever venture I work on next.

I’m asking myself things like:

  • Why do I get scared to publish things, to put myself out there?
  • What do I find myself doing when I don’t have to do anything with my day?
  • Do I still get up early, go to the gym, eat healthily, or do those only happen when I force them?
  • Do I want to be forcing myself to do those things? Why am I really doing them? What’s my relationship with self-discipline, and what do I want it to be?
  • For example, how is it that I’ve been able to build multiple successful businesses and yet sometimes can’t bring myself to get out of bed all morning? What’s going on inside me in that moment?
  • Why do I feel like I ‘should be’ being productive? Why do I see this period as a break between work projects—is work really the default? Why does it feel uncomfortable to be spending from a savings pot instead of a steady income? What other scripts are running in my head?
  • What do I love to do, how would I want my days to look, if I could design them from scratch? What’s stopping that from happening?
  • What areas do I believe aren’t ideal in my life, and what limiting beliefs do I have that are contributing to that?
  • I love the advantages that working remotely brings, but at the same time all my most fulfilling work projects have been together with other people, face to face. How do I reconcile that in my next venture?
  • And why do I find myself needing to answer all these questions? What am I trying to fix? What would it look like to just be, and to be OK with that?

The next chapters(s) of this writeup will explore how I’ve run those experiments and the weird and wonderful things I’m learning about human minds (and hearts and guts) along the way.

How long will I stay away from work?

Straight after the exit I said I’d take at least 2 months before the next venture. I also said I wouldn’t start something new until I felt drawn to. From a place of eagerness, not fear or force.

For 12 months I was very happy not working. Now, at 13 months, there’s one mission that’s starting to emerge. It excites me a lot, though it’s still not quite time to start.

In the meantime I’m planning to get a job in a café. I’ve been building businesses since I was 10 years old, this will be my first time working for someone else! But I love interacting with people, and serving, and I’d appreciate having some structure in my day.

And where have I been these last 12 months?

With no work responsibilities and more money than ever in the bank… you could say Life took me on quite an adventure last year. Silent meditation retreats and learning to dive and living on boats and waking up in a war zone and sex parties and airport romances and meeting Sir Richard Branson and bereavements and spiritual awakenings and…

I guess I hadn’t left the theme park yet.

Stay tuned for those chapters too.

  1. If it was making money without much effort, why was it bothering me so much? A friend helped me realise why. She was reflecting on a trip I’d organised for some friends. “Shai,” she said, “I really love how you go all out. You never do things by half.” I remembered my dad saying something similar too in a speech when I was a kid: “Shai believes that if something is worth doing, it’s worth doing right”. It explained why RightMessage was giving me the ick. I wasn’t keen to put my all into it any more, and being responsible for something that I didn’t care to put my all into—even if it was making money—didn’t sit well with that core value. 

  2. One thing that finally jolted me into realising it was reading The Six Pillars Of Self-Esteem by Nathaniel Branden. The first pillar is all about being willing to be honest with yourself about the current realities of your life. When I was quiet and honest with myself I knew that my narrative of “work’s going great” wasn’t true. Part of me knew I was muffling a foghorn deep within me: “this work isn’t fulfilling me”. 

  3. There’s a powerful lesson here. This is an extreme example of it, but the hardest part is always being brave enough to face the thing in the first place. You can cope with everything once it comes.