The Founder Mindset: 3 Places Pessimism Balances Optimism

Founders are all in.

They typically have large amounts of their personal wealth in the company, they have investors who have trusted them, sometimes even have personal assets tied up in the mix, they aren’t paying themselves market rate and they are making sacrifices in their personal lives.

It would be nearly impossible to not have a constant dose of optimism in order to stay the course (some may go as far to say delusion).

Optimism is surely a necessity.

But contrary to what may seem natural, so is pessimism.

In the wise words of Richard Feynman: “you must not fool yourself — and you are the easiest person to fool.”

As a founder, you really, really, really want the thing to work.

It’s a delicate balancing act, where pessimism serves to temper overarching optimism, ensuring a well-rounded approach to decision-making.

There are a few key areas that pessimism is helpful – let’s get into it.

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When Pessimism is the Hero

Optimism is surely needed as a founder. However, a healthy dose of pessimism in the right places can actually be helpful – here a three key places👇

#1 Customer discovery calls

  • In the early stages of solution development, customer interviews are key. During interviews, it’s easy for disappointment to creep in at this stage. If it does, a little alarm bell should go off in your head because it means you may no longer be doing customer discovery – you’re actually selling. Mike Vichich (Co-Founder & CEO of Pursuit) expresses a line that helps keep things in perspective at this stage: “It’s not customer discovery if you leave the conversation disappointed. That’s sales. So in the early days, you shouldn’t feel disappointed. Otherwise, it seems like you’ve got a solution that you’re trying to push rather than just understanding the problem.”

#2 Perspective and open-mindedness

  • Perspective and open-mindedness: A common piece of advice from multi-time founders is to keep an extremely open mind to all different possibilities of how to do things. Part of it is rooted in realizing how much you know and also do not know. As Mike Molinet (Co-Founder of Thena) expresses: “When you’re young or new as a founder, you know what you don’t know – you know you have a lot to learn. There’s then a phase where you start to see success and think ‘I know what I’m doing, I just need to execute.” But the perspective of realizing just how much you don’t know and how there are different ways of doing things is what will enable company growth to flourish.

#3 Contingency planning, prioritizing efficiency

  • Contingency planning and prioritizing efficient growth: If there’s anything these past few years have taught us, it’s the importance of efficient growth and how having a little extra padding for runway can be beneficial. Runway refers to the amount of time a startup can continue operating before it needs additional funding. Without previous necessitation, this has been a learning experience for many. As May Habib (Co-Founder & CEO of Writer) says, “this is much needed basic business 101 that a lot of people are learning for the first time – how to run an efficient business and how to grow efficiently.”

👀 More for your eyeballs:

Pavilion published their list of 50 CEOs to watch in 2024. We’re proud that 10 of the 50 CEOs are GTMfund founders! Congratulations to all the incredible founders on the list, and a special shoutout to our 10 founders:

  • Christine Cacioppo – Vanta.
  • Edward Chiue – Catalyst.
  • Alexa Grabell – Pocus.
  • May Habib – Writer.
  • Leena Joshi – CloseFactor.
  • Bob Moore – Crossbeam.
  • Maleka Momand – Esper.
  • Jaleh Resaei – Mutiny.
  • Prukalpa Sankar – Atlan.
  • Sam Senior – Testbox.

Notable News:

  • ZoomInfo finally got to visit onsite to ring the Nasdaq bell in Times Square, as its June 2, 2020 IPO was conducted virtually during the pandemic.
  • Google is rebranding its chatbot, Bard, in order to bring it into the broader AI family and more directly compete with OpenAI – Bard will now be called ‘Gemini’.

Levelling Up:

👂 More for your eardrums:

Andy Jolls is 25+ year executive with several years in CMO roles. As a full stack marketer, Andy has re-architected six brands and identities, and built three funnels from the ground up. He’s been a B2B leader in businesses from pre-revenue to $600MM. Andy co-Chairs the CMO group for Pavilion (6000+ GTM leaders) and is active in several marketing communities. Currently, he operates his own consultancy helping leaders with marketing strategy and AI in GTM.

In this episode, you’ll get insight on how to leverage AI with tactical use case examples, a three-step framework for leveraging AI in go-to-market, and career growth advice.

Listen on Spotify or find it anywhere you get your podcasts by searching “The GTM Podcast.”

🚀 Start-ups to watch: 

Closinglock: Announced their $12M Series A round. Closinglock provides fraud prevention technology to the real estate industry, modernizing transactions through a secure, easy-to-use platform. Read about their funding round (TC).

Spekit: Launched Spekit’s next-gen CMS and sales content experience designed by reps, for reps. This launch includes ‘sales content, one-click away’ and ‘content sharing & tracking with SmartSend.’ View the launch live demo on demand.

🔥 Hottest GTM jobs of the week:

  1. Mid Market Account Executive at Crossbeam (Remote)
  2. Director of Sales at Coast (NYC)
  3. Strategic Sales Engineer at Atlan (San Francisco)
  4. Marketing Coordinator at Matik (San Francisco)
  5. Sales Evangelist Content Creator at Writer (San Francisco or Remote)

See more top GTM jobs on the GTMfund Job Board.

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That’s it, that’s all. 

While I personally fall on the optimistic side, I recognize healthy dose of pessimism in the right places can be key to steering the ship.

While speed is a form of currency in the startup world, if moving in the wrong direction it can be futile. The true value of speed lies in its application towards the correct course—identifying the right path and then navigating it swiftly, ready to make informed pivots as the journey unfolds.

So I will leave you to the rest of your Friday with this: Direction, not speed.

Barker ✌️

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Before helping found GTMfund, Scott spent 4 years at Outreach as Director of Strategic Engagement. He was in charge of aligning key relationships with VCs, BoDs, ecosystem partners and community members to drive revenue and strategic initiatives across Outreach. Scott initially ran revenue/partnerships for Sales Hacker (which was acquired by Outreach in 2018). Prior to Sales Hacker, he led and built outbound Business Development teams at Payfirma and MediaValet. Scott also advises for a number of high growth start-ups and is the host/author of The GTM Podcast and The GTM Newsletter. At GTMfund, Scott leads all fundraising efforts and runs the media arm of the firm. He’s also responsible for assessing investments, team management, LP/community relationships and GTM support for founders.

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