Most SaaS founders chase the wrong signals. They obsess over user metrics and feature requests while missing the one indicator that actually predicts billion-dollar outcomes: unprecedented demand that feels unmanageable.
Chris Tottman learned this the hard way after building Message Labs from accidental discovery to £150M exit and then watching hundreds of startups as co-founder of Notion Capital.
He has decoded the difference between startups that scale and those that burn through millions while still searching for product-market fit. This isn’t typical VC wisdom, but it’s hard-earned intelligence from someone who’s lived through both the creative chaos of building breakthrough companies and the systematic discipline of scaling them.
Talking points include:
- How Message Labs went from a free feature to £150M subscription business in 8 years.
- Why 90% of companies never escape the discovery phase (and the signals that separate winners from wannabes).
- The “agentic revolution” reshaping SaaS development and what it means for human collaboration.
The Accidental SaaS Pioneer
Most SaaS origin stories follow predictable patterns, but Chris Tottman’s doesn’t. In the mid-1990s, while helping scale an internet service provider, his team stumbled upon something extraordinary: malicious code attacking email systems.
What started as a free security feature quickly revealed itself as liquid gold when they switched it on, and “the bell went off and this scream started to emit.”
That moment of customer desperation became Message Labs – Europe’s first major software-as-a-service company, serving 20,000 corporate customers before being acquired for £150 million.
The lesson learnt is sometimes the biggest opportunities hide in plain sight, disguised as customer pain points everyone else ignores.
The 90% Revenue Miss That Changed Everything
Success rarely follows the original playbook. Message Labs’ first go-to-market strategy – selling through indirect partners – failed spectacularly.
“We were literally 90% off plan. We missed our target by 90% in the first year,” Tottman admits.
The strategy was flawless, execution was solid, but it simply didn’t work.
This brutal learning mirrors what Tottman later discovered was Salesforce’s “second biggest mistake.” The pattern reveals a harsh truth: even experienced operators make similar fundamental errors.
The differentiator isn’t avoiding mistakes, but it’s having the “courage of your conviction” to pivot dramatically when reality contradicts your assumptions.
Beyond Product-Market Fit: The Discovery Trap
While most founders obsess over product-market fit, Tottman identifies a more fundamental challenge: escaping the discovery phase.
“Most opportunities never get out of discovery. They never genuinely find product-market fit,” he explains.
Even companies with £100 million invested can find themselves questioning whether they’ve truly achieved it.
The key indicators are unprecedented demand that feels almost unmanageable, combined with the ability to deliver consistently. But Tottman warns that product-market fit isn’t permanent – you can lose it. The real challenge becomes creating “highly repeatable” systems that can scale without breaking.
Listen to find out more about:
- Why AI will struggle to replace humanity’s “masters of collaboration” advantage
- The mathematical system behind social media growth (hint: it’s simpler than you think)
- How Notion Capital spots the next unicorns before they know they’re unicorns
Key segments of this podcast and where you can tune in to go direct:
[00:02:15] The birth of Europe’s first major SaaS company – how Message Labs emerged from chaos
[00:05:30] The 90% revenue miss and why indirect sales strategies fail
[00:12:00] How to know when you’ve truly achieved product-market fit
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Author
Adaline Lefe Mary John
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