Supercharging SaaS operators

Good morning, SaaS operators. I'm launching this letter for us today.

TLDR

1. We’re facing a fog of uncertainty like never before.

2. Economic headwinds, political, regulatory changes reshape how we operate.

3. Most ‘playbooks’ that worked last year don’t work today.

4. We need leaner structures and powerful mental models to respond.

We need to move with the urgency of a war room, but with the clarity and precision of thought of a boardroom. This letter will share stealth strategies that are working for us today, written in real-time by an exited founder, back in the trenches.

What you can expect in every letter

1. A challenge we’re facing right now.

2. A solution that’s working for us.

3. A tactical way to execute.

4. And the expected upside—strategic, financial, or both, if executed well.

All data used in analyses will be sourced. Scrappy tools we build to solve the challenge for ourselves will be shared.

Who is this letter for

You’re a CEO, CTO, COO, or CFO leading a SaaS company with $1M to $20M ARR—or aspire to be—and looking to build, scale, or sleep better at night, you’re in the right place.

Forwarded this email?

I’m Sanket 👋🏼 — I’ve spent 18 years building and scaling software businesses.

I founded and sold two businesses, then became an adviser to Fortune 500 executives on building and scaling software across U.S., Australia, and the U.K.

I’m back in the trenches, and recently founded Spring Street Capital—a committed equity fund buying and scaling vertical SaaS businesses. Entrepreneur.com recently highlighted how we’re “reinventing software exits.” 

In my spare time, I serve as a Coach for Entrepreneurship at The University of Chicago, helping students, faculty, and alumni build and scale software.

Operating a SaaS company has never been more challenging.

Economic headwinds, shifting buyer behavior, and a wave of political and regulatory changes are reshaping how SaaS businesses operate.

On top of that, AI is reshaping product roadmaps. Capital is tighter. Growth is harder. And the playbooks that worked last year don’t work today. The stakes are higher, competition fiercer, and the margin for error narrower than ever.

This letter will help you navigate this turbulence, scale your SaaS business, and combat uncertainty. My goal is to share real-time data, leaner structures, and powerful mental models my crew and I are using right now so we can all lead with confidence — even when the market (and the rules) keep shifting.

The ones I find myself best at solving, and others rely on me to help cluster across the four core areas of the business:

1. Leading

2. Growing

3. Optimizing

4. Deleveraging

These are the areas I spend most of my time when operating.

Uncertainty has increased the severity of impact when faced with these challenges. Mastering them isn’t optional anymore; it’s the foundation of building a SaaS company that will endure tough times.

I’ll share what was working, and equally important, what is not. I hope that over time, we can make this small group into something far greater: a force multiplier.

We will move faster, make better decisions, and build with greater confidence. Solving challenges together will unlock the leverage we never had alone.

I have always tried to be useful to builders; after all, you are my people. But I have three reasons why I'm consciously dedicating my time to this right now:

1. Rise in requests for advice: Operators I’m close to are burning out—texting, calling, reaching out in quiet moments of chaos. And I know they’re not alone. I feel a sense of duty to prioritize time for this.
   

2. Being useful is a discipline. I founded my firm, Spring Street Capital, to help operators—not for credit, not for ‘deals’, but because it’s the right thing to do. Showing up for operators is how we’ve earned your trust. Trust has built everything else. Being useful isn’t extra—it’s the job.
   

3. Giving back, after receiving so much. It’s not easy to will something into existence, and I hope whatever I can share from my own experiences can be helpful to you on your journey.

I spend my days speaking with top investors from Silicon Valley to Wall Street, and work closely with some of the best software operators in the world. This letter started because many have asked for it.

Some comments from builders and investors:

From a $10M ARR SaaS Founder & CEO

“You’re on a completely different level of thinking:

• You get to the root cause of my problems very quickly.

• Your solutions to my problems have literally saved my company.

• Raw, straightforward, no sugar coat bs, which I like, and founders need.

You need to share this with more founders so they can have a better time building.”

From a $7M ARR SaaS Founder & COO

“You’re one of the best operators I've met:

• Your speed and clarity of communication are incredible.

• I appreciate how you support and push simultaneously.

• You have a contingency for every possible risk before I know it exists.

I wish I had more access to you; I could really use it right now.”

From a VC of a Top-Tier Fund

“You're one of the few operators I trust running my portfolio company.

• The founder called me right after our call and asked to get you on a retainer.

• Whatever you're doing in convos gets founders fired up about building. I need you on more of my calls; keep doing that.”

It will take me some time to get this right, so please bear with me as I get my writing, rhythm, and cadence in order.

Cheers to building together,
—Sanket

P.S. If you’re facing a critical challenge, reply to this email with the summary of the problem. I read everything that comes through and aim to reply within 48 hours.