Learn the key lessons from Chris Tottman—Notion Capital co-founder, B2B SaaS pioneer, and serial entrepreneur—on harnessing Market Urgency, building a winning team, creating your own pond, and scaling
🌟 Hey there! This is a subscriber-only edition of our premium newsletter designed to make you a better founder and investor. However, I’ve decided to leave this one open for everyone to read because I thought it was just too good!
I met Chris about a year ago through a mutual friend.
At first it felt pretty crazy to be talking directly to one of the founders of Notion Capital, and since then I’ve been lucky to have the opportunity to know him better, pick his brain and learn a ton.
Needless to say I’ve learned at a really fast speed from both my conversations with him as well as from the way he acts.
I now thought it would be cool to share with you how his brain works (directly from him), so I asked him to answer some of the questions most “earthly” founders never get answers to.
About Chris’ life
Chris left school at 16 and hustled his way into the investment banking industry through an apprentice-type scheme.
Despite his family’s hesitation, he left banking after four years to attend two “boot camps” in sales and marketing because he had become fascinated with meritocracy and he believed it wasn’t entirely possible to achieve as an employee, where he felt he was outsourcing his future to a committee of middle managers.
By 24, Chris co-founded his first companies in financial services, teaming up with friends Richard Blundell and Paul Watson.
Soon after, he pivoted fully into technology alongside two close friends, Ben and Jos White, the founders of MessageLabs and Star Internet—two SaaS pioneers long before SaaS was cool.
The momentum didn’t stop there. With the success of MessageLabs (which scaled to $150M in annual recurring revenue), Chris and his co-founders realized there was a massive opportunity for B2B SaaS companies across Europe.
Instead of building just one more SaaS juggernaut, they decided to create a venture capital firm to fuel many.
That’s how Notion Capital was born—announced literally the day after MessageLabs was sold in the midst of the 2008 financial crisis.
Today, Chris and the Notion team have over $1B in assets under management.
Chris invests in new companies weekly and co-founds one business every six months.
He’s mantra is what he’s called the 4 Cs: Creating, Collaborating, Coaching and deploying Capital, and through these he is extraordinarily productive living the most plural of business lives.
1. What’s the most important thing founders should focus on when starting a new company?
Chris:
“I think founders have many different motivations—some want to ‘do good,’ others want financial independence, etc. But if you take those personal drivers out of the equation, my firm belief is you need to be solving a problem worth solving. That’s where what I call ‘Market Urgency’ comes in.
Market Urgency is about how ‘destructive’ or ‘painful’ the problem is for your potential customers. If it’s not painful enough to get someone fired or make them look bad—or if they can’t visualize being disrupted—then there’s little urgency to buy. You need to identify that painful kernel.
Often, founders start with one product idea but they don’t yet fully understand the market’s problem. By listening, asking questions, and being curious, you can uncover a problem that has the right level of urgency—one that compels people to act.”
Takeaway:
Validate your problem by measuring “how badly” it hurts potential customers. That urgency is the difference between a nice-to-have product and a need-to-have product.
In his book “The Go To Market Handbook for SaaS Leaders” Chris covers this in depth, via 10 chapters that all act as a Workbook for Founders & Teams to tackle each step pre PMF. As Chris says “you have a hypothesis and maybe some Lean Canvas” and the book is the perfect companion of what to do next.
2. When should a founder raise venture capital vs. bootstrap?
Chris:
“This one’s simple. You raise VC when you have more demand than you can support in a market that you can effectively own—so that you’re basically a market of one. If the demand can generalize into a huge market opportunity, and you can be the processing rails for trillions of transactions in that space, that’s VC territory. Otherwise, you might be better off bootstrapping.”
Takeaway:
VC money can be rocket fuel, but only if you need to move at hyper-speed. If your market doesn’t demand that acceleration (or isn’t big enough), external capital can become a distraction rather than a lever for growth.
3. How was founding Notion Capital? Any early challenges in building the brand and finding the best deals?
Chris:
“We sold MessageLabs in the midst of the global financial crisis (2008) and announced Notion Capital the next day. So we’d been planning Notion for some time.
MessageLabs was the first massive SaaS company to come out of Europe—$150M recurring revenue in messaging security. There are countless ‘campfire stories’ about that journey!
At the end of it, our thesis was simple: SaaS was only 1% of B2B tech spend, but we believed it would become 50%. That meant there would be thousands of SaaS companies disrupting the hardware, software, and systems integrator status quo. We wanted to either found or invest in these companies.
That is a 50x shift in spending habits - it was a mega trend just as AI is today.
We went the investing route—backed with $30M of our own money from MessageLabs—and raised our second fund three years later. Now we have $1B+ across 8 funds and invest from Pre-Seed to Growth. Our brand is built on the same principle: we’re entrepreneurs who have the bruises and scars to prove it. We empathize with founders at every stage.”
Takeaway:
Sometimes the best time to build something new is right after a major transition—like exiting a company.
Long-term vision (SaaS growing to 50% of B2B spend) can be an incredible north star for building not just one business, but an entire investment platform.
4. What’s different between the companies that raise $50M+ Series A rounds in months vs. those that struggle?
Chris:
“People forget it’s a two-sided market—on one side you have founders and their markets, and on the other side you have investors and their fund sizes.
Founders/Markets: Some founders and markets get ‘hot.’ Maybe it’s an in-demand AI solution or an already proven star founder. In those cases, you get 20 competing term sheets. Prices skyrocket, dilution is minimal, and it happens fast. Meanwhile, there are founders in less flashy spaces, or who lack name recognition, who might struggle to raise.
Investors/Fund Sizes: Every investor has a mandate and a fund size. A small fund under $50M looks for different returns than a $1B mega-fund. Each hunts in its own niche—by geography, by technology, by stage. A smaller fund typically invests smaller checks and is happy with smaller exits. A huge fund needs unicorns and decacorns to move the needle.
So, if you’re an unproven founder in a not-yet-hot market, raising from a mega-fund is an uphill battle. But if you’re a proven founder in a sizzling market, the mega-funds will line up to fight for you. Different segments. Different dynamics.”
Takeaway:
Recognize that “fit” matters between a founder, the market, and the fund’s size/thesis. Figuring out which investors align with your market, stage, and potential exit timeline can determine whether you’re in the “$50M Series A in a month” category or “struggling to raise” category.
What I’ve Personally Learned from Chris
1. Divergent Thinking vs. Convergent Thinking
Chris approaches problems from angles most people never see, which helps him uncover opportunities that others miss.
2. Create Your Own Pond to Swim In
Instead of operating under someone else’s rules, Chris constantly looks for ways to define or redefine markets so he can play by his own terms.
3. Collaboration Is Key for Success
Throughout his career, Chris has stressed that building together with the right co-founders, investors, and teams multiplies everyone’s chances of winning.
4. Creating Systems That Scale
From sales playbooks to go-to-market engines, Chris is always focused on building repeatable processes that can grow beyond any single individual. Fot that, leverage is key
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