During 2019, we launched a new podcast series, The Pain of Scale, it was something of an experiment to explore key challenges our founders face as they enter the unknown and set out out their extraordinary journeys. We interviewed nine experts on topics from leadership through to exiteering, and the thing that struck me most across those nine interviews was how much there is to learn, and how important it is to keep an open and curious mind.

Paul and I recorded a short retrospective of the series that you can listen to here.

I have picked one or two aspects from each episode that really struck a chord with me.

Building healthy leaders and high performing teams with Mike Snelling, Principal, The Table Group.

I’ve been a big fan of Patrick Lencioni, the founder of The Table Group for years. He wrote an incredible book called The Five Dysfunctions of the Team. And Mike and the team have turned those dysfunctions into a very effective and positive framework for leadership development that is as simple as it is powerful. Mike and his partners emphasise above all else the need for clarity, and Mike said something that really stuck with me, “You need to repeat something seven times before it really sinks in” and that’s really stuck with me. I’ve started to use that in my work, to really pare back the way I think about and communicate my role at Notion.

The second thing I took from Mike’s interview was the need for “stillness”. He argued that the best leaders work themselves to such a point of clarity that they achieve an air of stillness. And I think that’s incredibly powerful, that sense of comfort you get when you know that a leader has a total sense of clarity of what needs to be done, has a team they trust, and has all the necessary resources at their disposal. He talks for the need to not overcomplicate, to quiet things down, focus on delivering on your objectives. In a way he’s saying that you almost retreat into yourself, quieten down the noise and focus on what’s important.

Why founders need operators (and why artists need scaffolders), with Maureen Taylor, founder of SNP Net.

Maureen has been advising some of the greatest tech founders of some of the world’s best known tech brands for decades. And she is a powerful advocate for the importance of the duopoly of the founder and the operator.

She describes technology founder as the creative force, who is creating something from nothing, just like Michelangelo, who of course painted the roof of the Sistine Chapel the 1500’s. And when you go into the Sistine Chapel and look up, you are struck with a simple thought. How? How did he do it? How did he get all the way up their and create such a work of art? Well, part of the answer is he had the most extraordinary scaffolders! So just like one of the greatest artists the world’s ever known, needed the most extraordinary scaffolders, the best tech founders need incredible operators.

Category thinking, with David Peterson, of Play Bigger.

This episode reminded me of how comforting it is to be in a conversation with someone who just exudes confidence in their topic. And on Category Thinking - design, development and domination - Dave has that in spades.

Category thinking is really important for tech entrepreneurs to embrace. If you boil down the essence of a tech start-up, you are invariably doing something no one has done before and therefore it is incumbent on the founder to define the industry you are creating. And that is what category thinking is all about. And Dave - who lives in California - uses the simple story of a friend asking what car they should drive into the mountains to go skiing. And you don’t say a Jeep, or a Land Rover, but rather an SUV, which defines the entire category of suitable cars. That’s what category thinking is all about. That is the mindset you are trying to create. Companies are carving out new curves, that redefine an entire industry.

Talking the science of sales with Jacco Vanderkooj, Winning by Design.

Our fourth episode was with the force of nature in human form, that is Jacco Vanderkooj. It’s hard to overstate the role Jacco and his team are having on the professionalising of SaaS sales, on the planet and within our portfolio. And the very best companies in our portfolio - companies such as Tradeshift and Gocardless are working with WBD to improve their sales capabilities.

Two things from Jacco really resonated with me.

1. Think about impact. We get very hung up on long term value, whereas Jacco is focused on impact today. Sell on impact today, deliver on that impact today, not value tomorrow or next year.
2. Going from founder led selling to team based selling. And if a start-up can make that transition, they know they are well on the way to unlocking predictable and scalable growth.

Building the product machine with Carlos Gonzalez-Cadenas, CPO, Gocardless

Carlos is one of those people who encapsulates the mantra, “If you are going to think big, think bigger”. He’s a successful founder in his own right, now CPO at Gocardless, and he talks incredibly powerfully about the importance of building a product machine, that allows a business to innovate with machine like precision as they work through three critical phases:- proving viability, scalability and durability.

We are seeing him drive that transformation at Gorcardless, building breadth and depth of capability in their vision to create the world’s bank to bank payment platform.

Pricing as the exchange for value, with Patrick Campbell.

Pricing is one of my favourite topics, and Patrick is favourite person to talk to about it. This is an area that we as entrepreneurs and venture capitalists really need to get better at. We need to grow up, and learn more about micro-economics, and pricing theory, understanding price elasticity and willingness to pay, understanding supply and demand curves. And I don’t know anyone in our industry who knows as much about this topic as Patrick and I learn so much every time I talk to him.

One thing Patrick is very good at is encouraging people to not be afraid about pricing and in particular to not be afraid of talking to their customers about pricing and willingness to pay.

Asia, a beguiling destination for european entrepreneurs, with Susie Hughes.

Susie Hughes has an incredible perspective on the tech ecosystems across Europe, US and now Asia, having lived and worked within the tech scene in San Francisco, London and now Singapore.

We think of the US as being homogenous market - even if there are differences by states; we think of Europe as being heterogeneous - but there is political and economic cooperation. But across Asia, there is very little in the way of cohesion and the individual countries and cities are very different, and Susie is an excellent guide.

Raising venture capital as fuel for you SaaS machine, with Beth Ayers.

Beth was the SVP Strategy at Newvoicemedia, and was at the forefront of their fund raising at Series A, B, C and D through which they raised more than $100m. And she she really thought about that journey, and what I liked in particular was her message to founders to never forget they are building a machine. And that machine runs on certain fundamental principles: cost of acquisition, average contract value, gross margin, retention and revenue expansion. The later stage investors understand this inside out, but at an early stage, while you may not yet have all the data you need you must be able to demonstrate that you understand these topics, how the machine works and are collecting the data to be able to answer these questions as you grow.

Taking control of the exit process with Ian Milbourn.

The last episode in our series was with the extraordinary Ian Milbourn. Ian is a partner at Notion and is a deal junkie. And he supports our founders on M&A and on exits. And his focus on “exiteering”, which for us encapsulates the sense of readiness to be acquired at any time, even if the exit may well be years off is very powerful.

Three things for me stood out:-

1. Ongoing DD assessment
2. Understanding your universe of acquirers and the rationale for why they would buy
3. Building a network of advisors who can educate and support you on a transaction

So what did I learn through this podcast programme? I learned that I know a lot of people who know a lot of people who know a lot of stuff that is very important to us and our founders.

I hope you’ve enjoyed listening to these podcasts as I’ve had recording them.