SaaS

9 Brutal Truths About Startups I Know After 20 Years in SaaS

Rob Walling
Rob Walling•Jan 4, 2026

Original Description

SaaS is an incredible business model, with recurring revenue, high margins, and big exits. But there’s a dark side most founders don’t see until it’s too late.
In this video, I break down the uncomfortable truths every founder should know before they dive in.
Links in the video:
Join the Mastermind Matching Program: https://microconf.com/masterminds
Watch more videos like this 👇
If I Had To Start Over, Here's 3 Steps I'd Take to $1M+ Revenue: https://www.youtube.com/watch?v=3qUJnFyRlyQ
NEVER Make These 6 Mistakes (Lessons from 20 Years in Business): https://youtu.be/b56OA6yGT5A
STOP Building Your Audience (Do THIS Instead): https://youtu.be/n_CEYs1TUiE
About Me:
I’m Rob Walling. I’ve been building, growing, and acquiring SaaS companies for nearly two decades. I’ve started six companies (five of them bootstrapped) and exited multiple times, most notably selling Drip in 2016.
I’ve invested in over 200 startups, and my focus is on helping founders build multimillion-dollar companies without the pressure of the traditional "unicorn or bust" venture capital model.
🚀 Scale Your SaaS with TinySeed
If you are a B2B SaaS founder looking for funding, mentorship, and community, check out the accelerator I co-founded. We designed it specifically for bootstrappers. Apply to TinySeed: https://tinyseed.com
🤝 Join the Community at MicroConf
I co-founded MicroConf to create a space for non-venture-backed startups. Connect with thousands of other founders, watch world-class talks, and find the support you need to grow your business. Explore MicroConf: https://microconf.com
🎙️ Listen to Startups for the Rest of Us
Check out my podcast, where I’ve shared insights on bootstrapping and growing startups for over a decade. With over 800 episodes and 15 million downloads, it’s the longest-running podcast for software entrepreneurs. Listen here: https://www.startupsfortherestofus.com
📚 My Books on Startups & SaaS
I’ve written several books to provide tactical advice on launching, growing, and selling your software company:
The SaaS Playbook- My guide to building a multimillion-dollar startup without venture capital. https://saasplaybook.com
Exit Strategy: The entrepreneur's guide to selling your business without regret (co-authored with Dr. Sherry Walling): https://exitstrategybook.com
Start Small, Stay Small: A developer's guide to launching a startup: https://startsmall.com/
The Entrepreneur's Guide to Keeping Your Sh*t Together: How to handle the psychological pressure of being a founder (co-authored with Dr. Sherry Walling): https://saasplaybook.com/order/p/entrepreneursguide-ebook
👋 Connect with Me

Comments

Want to join the conversation?

Loading comments...