A little while back on LinkedIn and Twitter we put together a list of things that later, once you are successful, even very successful, you’ll regret. It got a lot of engagement from the SaaS veterans out there, so I thought it would be worth digging in more on each point.

Regrets are different than mistakes. You will make so many mistakes. We all do. You learn, you move on.

No, regrets are things that especially in recurring revenue companies, you’ll look back and say … well, I knew I should have done that at the time, and it wasn’t crazy hard, and it would have helped a lot … but I still didn’t do it. The flip side of recurring revenue is you will later regret things that you could have done earlier to help, that were sort of obvious, that would have helped more of it recur. Because later you’ll see just having gotten on one more jet, made one more key hire, and then a few years down the road, you might be $1m, $2m, $5m further along in ARR. It Compounds.

So there’s one topic you have to be ruthlessly honest about as a founder: are you falling out of product-market fit?

The reason you have to be ruthless is while sometimes falling into product-market fit can happen relatively fast, e.g. with a magic feature … falling out takes time.

It takes time for customers to churn, especially bigger customers, and especially customers that sign annual deals.

It takes time for your brand or even just your mini-brand to stop carrying you into deals.

It can take years to truly fall out of product-market fit. Or at least — to truly see it clearly.

So the #1 OG vertical SaaS leader is Veeva. A core CRM, data and Cloud platform for the life sciences industry, it started off as a “Salesforce for Pharma” and expanded from there.

It raised less than $10m before it IPO’d, and fast forward to day, it’s at $2.5 Billion in ARR, and is very profitable (almost $1B in non-GAAP net income), but growth has slowed to a mature 12%.  Still, Wall Street is good with the combo.  It trades at a stunning $32 Billion market cap.

What’s the toughest part of running a startup? A partial list:

• Recruiting. This is always hard, forever.
• Co-founder Conflict. Hopefully, you don’t have this.  If you do, boy it’s hard.
• Almost running out of money. Happens to almost all of us. Not fun.
• Loneliness at the top. Tough indeed.
• Having to rebuild the team every few years. Man.
• Falling behind the competition. Painful.
• Losing momentum. It’s so, so hard to get it back.

That’s a lot of tough stuff.

But one visceral memory I had was of a celebration dinner with friends after Adobe acquired my last startup. I was so tired, I barely made it to the restaurant.

And then I had to choose between 3 open parking spots. But I couldn’t chose. I just sat there.  

It had been 5.5 years of mission-critical decisions. Many of which I got wrong. I just didn’t want to, I couldn’t, make those decisions anymore.

So this is the time of the year when founders step down. Often quietly. Folks recover a bit from the end-of-year push, reflect, and sometimes … decide it’s time to bring in someone new. A CEO to take things to the next level. Etc.  And even more of us think about it. Heck, I’ve thought about it several times over the years.

I always try to talk founders out it handing over the reigns. I always try to tell them that 95 times out of 100, a better answer is to find a strong COO or similar to help carry the load. You know so much, after all.

But sometimes, it’s just time.

When it is, then I just have one more bit of advice — You May Be Asked Back. They often shake their head No, but trust me.

Some recent-ish examples of founders coming back as CEO:

* Therese Tucker, back as CEO of Blackline
* Josh James, back as CEO of Domo
* Eoghan McCabe, back as CEO of Intercom

There are many others. CEOs will come and go. But as a founder — you are a founder forever. That title, that knowledge, that passion, and that connection can’t be taken away. And the team may need you again.

At SaaStr AI Day, Mike Tamir, Head of AI at Shopify, and Rudina Seseri, founder and Managing Partner at Glasswing Ventures, level-set about where we are in the cycle for Enterprises adopting AI and the critical work being done at Shopify to leverage AI and solve real problems.

Mike and Rudina do a great job of explaining the complex AI terminology for everyday non-technical founders and leaders to understand and apply to their businesses. Today, many initiatives in AI are mostly superficial, with limited impact on a dollar basis. At Glasswing Ventures, they tell their AI-native companies not to lead with AI because it’s such a superficial indication of interest.

On an adoption basis, there have been some “green shoots,” particularly with Klaviyo and the impact they’ve had bringing AI from a project siloed or customer interface level and into their core business where they’ve automated 700 humans and over two-thirds of their customer success. Why is Klaviyo noteworthy? Because they’ve contributed $40M to their bottom line by bringing AI to their core product and business, and they’re one of the few companies who have.

• SaaStr 736: What I Learned Selling My Company for $130M with Harry Glaser Founder of Periscope Data and ModelBit

• SaaStr 735: How to Navigate the Shift to Generative AI with PagerDuty’s CEO Jennifer Tejada

• SaaStr 734: The Latest in Series A Rounds, AI Growth Rates and More with SaaStr CEO and Founder Jason Lemkin

Listen on Apple Podcast, Spotify or Google Podcasts

Be kind

To your coworker that made a mistake, even a big one

Be kind

To your cofounder that was great for a while, but just can't go much further

Be kind

To your boss that did great things for you, even if later they took advantage Be kind

To the ones that tried

I know it may not be what you want to hear

But the answer to how to get through tougher times

is generally to work even harder

At least for a while

Founders: when the round closes, send everyone that bet on you a personal Thank You email

Yes, maybe they were lucky to get an allocation

But … they bet on you for a decade

That quick email goes so far.

And is so … rare.

© SaaStr 2024

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