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Why It’s Easier for Second-Time Founders to Raise Venture Capital. Even With Nothing Even Built Yet.

SaaStr

Dear SaaStr: Why Is It So Easy For Entrepreneurs With Previous Success to Raise Funds From VCs for Their New Venture Despite Not Having Domain Expertise? As Dharmesh Shah co-founder and CTO notes in the SaaStr Annual deep dive below, the second time … they just really wanted to go big. It doesnt necessarily work better.

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Dear SaaStr: Is It OK Just To Do Things Yourself as a Founder?

SaaStr

Early on, especially before you’ve hit product-market fit or when you’re trying to figure out what’s broken, there’s no substitute for rolling up your sleeves and diving in. It’s also often true as you are entering new markets, or selling new customers. Even if you’ve hired someone to do it?

CTO Hire 209
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M&A Is Back! Melio’s $2.5B Exit to Xero — In Just 7 Years!

SaaStr

Learning #4: Israeli Tech Talent + US Market Focus = Winning Formula Melio’s 600+ employee split (200 in NYC, 400 in Tel Aviv) optimized for both market proximity and engineering talent density. But context matters: Market timing : Fintech valuations compressed 60-80% from 2021 peaks Strategic premium : 13.4x

Payments 227
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3 Ways I’ve Changed Venture Investing at SaaStr Fund

SaaStr

– RevenueCat now powers 1/3d of all new mobile subscriptions world-wide – New Apps using RevenueCat doubled in last 6 months – Powering monetization for ChatGPT, Notion, VSCO, Runna, and pic.twitter.com/McFmCBZ0eE — Jason SaaStr.Ai It’s too fast today in almost every segment.

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The Top 10 Reasons to Attend 2025 SaaStr Annual, May 13-15 in SF Bay!!

SaaStr

Speakers share their playbooks on everything from achieving product-market fit to optimizing CAC:LTV ratios and scaling go-to-market strategies. SaaStr Annual attracts thousands of high-quality SaaS professionals across functions like engineering, product, marketing, sales, and customer success.

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How SMB Digital Brands Can Win the Best Talent

FastSpring

If you have the CEO, CTO, some executive chat through, here’s the big picture of the company. Why are you looking for a new job? Let’s find a new shirt. Lizzie Mintus (07:58) Yes. Yeah, it happens all the time because the small company cares about you, David, as a person. Here’s your impact.

SMB 107
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Lessons Learned Rolling out AI Agents to 16,000+ SMB brands with Gorgias’ CTO

SaaStr

The beta phase involved 50 brands and the creation of a playbook for activation, which was a collaborative effort between the product marketing team, success team, and others. The models used by the company are changed often, with different steps having different models, and the team tests something new every week.

New CTO 167