Interesting Views: a spotlight on Chris Tottman from Notion Capital and Included VC

Interesting Views: a spotlight on Chris Tottman from Notion Capital and Included VC

Editor's note: this is a syndicated post from Views, a fresh interview-focused newsletter from tech enthusiasts Pol Fañanás and Gerard García. This interview with Notion Capital co-founder and GP Chris Tottman was first published here.

Chris Tottman is currently co-founder and General Partner at Notion Capital, London-based early stage VC investing in European B2B SaaS and enterprise tech with $500M+ AUM and 60+ investments such as Tradeshift (B2B commerce platform, $661M funding by Goldman Sachs and GP Bullhound, among others) and GoCardless (B2B payments, $122M funding by Accel and GV, among others).

Chris is also a co-founder of Included VC (together with Nikita Thakrar and Stephen Millard), a new Venture Capital (VC) Fellowship with the mission of changing the face of the VC industry, dramatically increasing diversity and maximising funds success by transforming networks, staff, dealflow and investments. To do it, Included VC empowers diverse outliers with potential of having significant professional and social impact in venture capital and startup worlds through education, networks, mentoring, executive coaching, investment committees, career workshops and in-person retreats by tier 1 VCs officially supporting and funding the initiative.

Included VC partners have a total $3.5B+ AUM and 320+ exits and include some of the best players in the Venture Capital game like Creandum ($800M AUM), Daphni (€165M AUM), Enern (€250M+ AUM), European Investment FundK Fund (€285M AUM), M12 Microsoft VenturesMangrove ($1B AUM), Mouro Capital ($400M AUM), Notion Capital ($500M AUM), Seedcamp ($200M AUM) and Wilson Sonsini. They account with brutal early stage investments in their portfolios like Spotify (IPOed, $62.3B market cap), iZettle (acquired by PayPal for $2.2B), Skype (acquired by Microsoft for $8.5B), (IPOed, $13.8B market cap), UiPath ($1.2B funding raised, $10.2B valuation) and Revolut ($917M funding raised, $5.5B valuation).

Previously, Chris was an early team member and Chief Commercial Officer (CCO) at MessageLabs Group (Messagelabs & Star Internet), messaging security company acquired by Symantec for $700M. There he had multiple roles and helped the team go from ideation to creation and ultimately to domination of a new product category while growing from zero to $200M+ revenues, 1000 people team, 10M users and 20k customers.


Could you give us a brief intro about you and your origins?

Working-class kid from the East End of London. Classic background of 1000's hours of sports and the less school the better. At 17 I managed to get on a pathway program into the City (investment banking in London) the year before the big bang of de-regulation of UK financial markets. This was followed by a huge influx of M&A and overseas firms buying up UK stockbrokers and investment banks, the stock market collapse of 87 and huge restructuring and redundancies that followed.

This happened all before I was 19 and although I loved every minute of it, after 5 years I knew I was more interested in pure meritocracy than being tied to a desk in a suit like a cog in a clock. I gave it all up to learn sales in a commission-only environment which provided the paired down rawness I felt I craved (much to my parents disappointment). For me, it provided a forcing mechanism to challenge how your attributes convert to skills and how those skills convert to brand, reputation and monetisation - the purest form of meritocracy without the safety net of all the bullshit we tell ourselves in a job with a boss. I then started my first company at 25 and have never looked backwards.

Now 51, having founded with 4 long term business partners 11 years ago, I get to invest in some remarkable people in B2B cloud technology startups and work with them on scaling their businesses.

What would you say has been the biggest win in your life?

Giving up each career and industry every 8 years and starting again.

Related to the above, and your biggest failure?

The year after I give up a career and I have started again feels like the biggest mistake of my life. Cracking the code of the new industry I am in is extremely challenging before clarity emerges. But I have come to realise that it is human nature and that if I surround myself with the right people and challenge (often privately) everything I am told then unbelievable opportunities emerge to build something with a significant point of difference. Of course, some time just telling yourself that "the more that I fail the more successful I become" is a false mantra but generally I am closer to success the more calculated risks I've taken which typically requires failing before succeeding.

What is your ideal founder profile?

I don't really have one and it wouldn't be a stationary definition if I did. I'd say it's people with significant gravity, maybe misfits or perpetual winners, people hard to please, generally insecure, unsatisfied and restless with the ability to make rational people do irrational things.

The biggest question I have is "do I want to build a massive and enduring business with this person?" because frequently building massive companies from nothing can be a miserable experience fraught with challenges, well beyond the limits of peoples experience.

Overcoming these challenges is not something success negotiates with. Success demands you overcome them or success walks away. So "how will this relationship work when it is all fucked up" is clearly important to understand to get into the right relationship with the right people. That's critical to the Founder, myself and all the other stakeholders. There is no better drug in business than winning and so getting into the wrong relationship is fundamentally a miserable experience not forgetting how expensive it is in losses.. and lost opportunity.

What is your ideal investor profile?

Founders / operators who are committed angels or run a fund. Having a conversation with someone with operational chops is significantly superior than with an investor with none. Then it's VCs with deep pockets who aren't dicks.

What present and future markets are you most interested in?

CX. 99% of enterprise consumer experiences are terrible as the majority of the biggest enterprises outsource how they support customers. So the moat when you solve enterprise CX for the most demanding of consumers of businesses is massive. I call this B2B2C.

Could you share with us 3 startups you like and why?

  • Unbabel. Building the translation layer of the internet so that the biggest brands in the world can support their global consumers in their native language using Unbabel AI at a fraction of the cost of hiring local language experts. Language is one of the biggest issues for globalisation that is almost entirely solvable by tech yet isn't. My bet is Unbabel will solve a significant piece.
  • Beam. They enable some of the most vulnerable people in society get back into work and gain financial independence. They are able to do this at an extremely higher rate than existing non-tech solutions which cost the state £30k per person per year. From a mission perspective it's harder to find a more mission-driven founder and a more noble mission - providing vulnerable people with the means to be independent.
  • Easol (previously named Fixers). Experiential Travel OS for Enterprise and Small companies delivering experiences. Experience Commerce is close to $T annually and no brand in technology owns this space. Like none! Weird! The company’s revenue was devastated by lockdown after growing 50%+ MoM and so I invested 5 years worth of burn into this amazing husband and wife founding team so they can rapidly build out their product in this quiet 2020, in readiness for the recovery.

Note from Pol & Gerard: If you would like to provide life changing help to homeless londoners, through tech based scalable solutions and top support network you can easily find and fund homeless people to help them start again, acquire valuable training and succeed in new careers to build a better future.

Could you share with us 3 investors you like and why?

  • Maria from BeaconLike me she's an outsider with huge mental energy but unlike me she's an extremely detailed thinker. When we work on a company together it is like working with the two sides of a brain but in two separate heads. Left and Right brains working in synergy, off the charts learning experience.
  • The three investors at NotionStephSusie and KamI just cannot function with their graft, insights and frequent inspiration. Spoiler alert - hire unbelievably great people, give them abnormal levels of autonomy and cheer their failures as much as their successes. Venture is a game for winners who spend most of their time losing, never forget that.
  • The core investors on the Unbabel board work really well. I led the A round, Andy Vitus from ScaleVP led the $20M+ Series B and after that a Tier 1 US firm attempted to add a 1x participating pref on the day of signing the Series C (we’d had 5 offers and were massively over subscribed, obviously we told them to jog on). Finally Sri of Point72 led the Series C. The investor dynamic is fantastic - smart, empathetic, diverse backgrounds, high simulation skills and pattern recognition. All the firms have tremendous resources to work with the founders and execs.

Who you have round the table and what they can do between meeting makes a massive massive difference. How they can do it too.

What are the 3 books you feel everyone should read and why?

I tend to read from my book clubs but mostly to work on myself, I believe we are our worst & only enemy. I'm wired in such a way that I can hold many opposing views simultaneously & link often entirely unrelated information and concepts together to establish new insights. I think of this as a simulation skill & so books fuel this significantly. My entrepreneurialism comes from this ability to simulate information and mash it together back and forth for many many years until POP! Something valuable appears almost unexpectedly.

  • A fascinating read for me is the Power of Two by Joshua Wolf Shenk. I don't see myself as an independent entrepreneur. I am very codependent on others and I do everything in partnerships or triumvirates. This book explores the historical partnerships like Lennon and McCartney & so very insightful about something important to me at a deep level of how people and teams function. Of course this can also be related to founders, ideation, start ups, teams and how we self organise.
  • Anything written by Matthew Syed. I particularly recommend Bounce to Teenagers as it simplifies the basics of being successful: 10,000 hours of practice and who you practice with. If I wanted to adapt that oversimplification. Outworking all around you, in something you love and working with increasingly better and diverse people - for me this is transformative to leading a successful life. Happiness requires something more but that's for another day. And I believe that makes up for a good combination with “Range: Why Generalists Triumph in a Specialized World” by David Epstein, since on the one hand you have the previously mentioned importance of focused work in what you love as key to success while at the same time understanding that high performers also leverage the power hidden in the balance with an approach based on thinking broadly and embracing diverse experiences and perspectives. Two somewhat conflicting arguments but it is precisely in the combination where your superpowers. live. The un-tapped potential of people and teams is one of my geeky areas, where I can be a total obsessive and a bore.


Could you walk us through your experience being the CCO at MessageLabs and leading commercial efforts to go from 0 to $150M+ rev, 10M users, 20k customers, 1000 people team and eventually selling the company to Symantec for $700M? What key lessons did you learnt in this successful scale up and exit?

I think the biggest challenge was that we were 90% off-plan in year 1 which is never a comfortable place to be. Flawlessly conceived strategy based on all the available data & evidence. Great execution. But didn't work. Wouldn't work. Never going to work.

VCs were pretty frustrated (under-statement). We shifted from 100% indirect to direct with indirect fulfilment. To many, this doesn't sound very different but in GTM terms it can make all the difference. We let go 65% of the Sales team and hired what ended up being 3 rockstars in a month who led many parts of the business beyond the Exit.

So by grasping the nettle, making major changes and hiring game-changing people we started to crush the numbers. The scaling issues arrived at an alarming pace and we actively looked for them. Cracking the US, then several international markets, pricing, shifting the positioning and messaging, new products and low-cost competition eroding margins and LTV.

I rarely made a big direct contribution to many of the solutions to these challenges because I focused on hiring and working with remarkable people and having an influence on some things versus micro-managing people and other aspects. MessageLabs grew at twice the venture speed, $150M in 8 years vs $75M but we were still frustrated by our lack of growth every day. We were very "C minus can do better". I think that mindset is critical too.

Of course now at Notion we have a dedicated platform for all these scaling issues that our Founders can plug into but in 99 SaaS wasn't really even a phrase.

About lessons, some are already mentioned but at the end of the day all founders are basically pioneers making something out of nothing in extraordinary harsh conditions. The most successful ones are bolder, have a higher risk appetite, can perform and evolve rapidly under sustained pressure and they are able to make increasingly more successful people with greater pedigree do illogical things like join or invest in their company. We like these crazy people, good at solving problems never solved before.

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