From Operator to Founder

In 2023, I became a true co-founder for the first-time. While I have many early startup experiences (XUMA during the dot com, Salesforce pre mainstream cloud, Zuora as an early SaaS app, Ayasdi early unsupervised machine learning, Elastic early open source and open core), the last 20+ years have mostly been spent operating, scaling, and leading teams and organizations.

Here’s my reflections on what’s been different for me as an operator vs. founder: 

1. Capital

• Operator: More is required. Your job is to scale the business and go after the market opportunity in the biggest way possible.
• Founder: Less is better. You want to limit dilution and raise only what is required to get v1 out to your early beta customers. Be scrappy.

2. Product 

• Operator: The How. Your job is to figure out how to get your product into the hands of as many customers as possible, fast. 
• Founder: The Why. Your role is to figure out what you are building, why the world needs it, and how it solves a big pain point today.

3. Culture 

• Operator: You build it. Your job is to help build the right culture by hiring the right people. You operate and lead by example. 
• Founder: You own it. You own defining every aspect of culture. It’s every word or phrase you use and the full company experience matters. 

4. Hiring 

• Operator: Next 10. You are always thinking about the next 10 hires. Who do you need to hire 3-6-12 months out? 
• Founder: First 10. You own identifying the first 10 hires,  and mapping out how individuals are must-haves now and in the future.  

5. Operating

• Operator: Get Work. Work is your operating DNA. New work is constantly distributed from the top and across the org. 
• Founder: Find Work. Work is limitless, your job is to define work and what is required from Day 0 and beyond. Never stop finding.

While the allure of starting something has always been there for me, taking this leap of faith in 2023 required many things to fall into place. 

• Right Timing: Personal, family, and finances. Risk tolerance. The choice between CxO share % allocation vs. founder ownership. 
• Right Pain: First-hand experience. $100s of millions spent over the years to solve it unsuccessfully. A strong conviction that I can help fix. 
• Right Market: A down market and starting anew before an upswing. Early tectonic shifts – like on-prem to cloud – that will enable 10x+ future growth. 
• Right Team: Finding co-founders with shared values, trust, and diverse experiences. Alignment to build a small, elite team vs a massive army.  
• Right Network: I am humbled and thankful to the many 100s of people who have given me their vote of confidence (including angels). You all rock. 

Finally, two shout-outs as doing this today would not be possible:  

Aaron Katz - You referred me to Salesforce and Elastic. You then took the ‘founder’ dive after many years of operating. We fly fish together, we operated at scale together, and now we build things as founders.  🙌

Tien Tzuo - As your first hire at Zuora, I got to do everything. Now all those pre-product conversations and late evenings at Salesforce come to bear, as well as the learnings from all of those decks, product launches, and more. 👊

Excited for 2024 and look forward to unveiling what’s next later in the year!

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