Sahil's Recent LinkedIn Posts

My first project at IRS is live: You can now sign up for refund email notifications within http://irs.gov!

Exciting news: after 14 years, I’m stepping down as CEO of Gumroad. I’ve found the perfect leader to take over for me: Ershad Kunnakkadan. (While he just moved to NYC this year, he’s been with Gumroad remotely for 8 of those 14 years.) He’ll run Gumroad differently, and we’ll restart our quarterly public board meetings in Jan 2026 (I remain the board) so everyone can learn alongside us as we make this transition. As always, let me know if you have any questions!

Now at Internal Revenue Service!

Check out the new Gumroad office at our open house, Thursday March 26.

What Elden Ring Taught Me About Building a B2B SaaS When I first picked up Elden Ring, I wasn’t expecting it to give me lessons I could apply to my day job in B2B SaaS. I thought I was just signing up for a tough but beautiful open-world adventure. But after 100+ hours, I realized that the way FromSoftware builds an immersive, challenging, and addictive experience has surprising parallels to creating and scaling SaaS products. 1. Your users will figure things out if you give them agency Elden Ring is famous for its lack of hand-holding. No “go here” arrows. No endless tutorials. Just a vast, dangerous world and the tools to survive in it. In B2B SaaS, the instinct is to over-explain everything — but customers often don’t need an on-rails experience. Give them intuitive systems, empower them to explore, and they’ll uncover your product’s value in ways you couldn’t script. 2. Difficulty is not the enemy — frustration is In the game, hard bosses don’t cause rage-quits when players feel they can win if they learn the patterns. The same is true in SaaS onboarding: complexity is fine if it’s purposeful, but confusion with no clear path forward is toxic. Your role is to challenge, not to alienate. 3. Player (customer) stories matter more than your own Every Elden Ring player has “their” story: the boss they finally beat, the weird build they tried, the hidden path they found. In SaaS, you want customers telling their success stories, not parroting your feature list. Your marketing should be a chorus of customer wins, not a monologue of product specs. 4. Optional content can create super-fans Much of the game’s best content is completely optional — secret bosses, hidden dungeons, and cryptic NPC quests. That’s the SaaS equivalent of advanced features, power-user workflows, or deep integrations. Not everyone needs them, but the ones who do will become your champions. 5. Community is your greatest force multiplier Players rely on each other — sharing tips, making memes, and warning about ambushes (“Try finger, but hole” — if you know, you know). For SaaS, your user community can onboard each other, share best practices, and uncover use cases you never imagined. 6. Iterate like patch notes FromSoftware didn’t get the balance perfect on day one. They adjusted drop rates, tuned enemies, and refined mechanics based on feedback. In B2B SaaS, releasing is just the beginning. Listening, iterating, and patching quickly is how you earn long-term trust. Elden Ring taught me that building something challenging, rewarding, and worth exploring requires trust in your audience, patience in your process, and the humility to keep refining. In other words: whether you’re slaying dragons or scaling ARR, it’s about creating worlds worth staying in.

What are the best books you’ve read on navigating bureaucracy?

What’s your favorite cheese

Antiwork / Gumroad's 2026 public annual meeting – financials, team changes, product highlights, and a Q&A with investors https://lnkd.in/eXE4r6Af

What GPT-5 taught me about b2b SaaS 👇