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SaaStr Q&A

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Blog Posts, Early, Hiring, Leadership, Q&A, Sales

Dear SaaStr: For High Dollar Vertical SaaS, Does The First VP of Sales Need Domain Expertise?

Dear SaaStr: If you were hiring a head of sales for a high-priced, niche B2B SaaS product, would you focus on general B2B SaaS sales experience or on market/customer knowledge, assuming it will be very difficult to find a candidate with both? This is the scenario when the trade-off is the most acute. Imagine you…
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Blog Posts, Q&A

How To Take Care of Yourself As a Founder

Dear SaaStr: How Do You Take Care of Yourself As a Founder? Quiet quitting, feeling sorry for yourself, working 30 hours a week, etc. — that doesn’t really work for a founder. It may feel good in the short term, but it doesn’t work. It doesn’t get you to success. But you do need to…
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Blog Posts, Career Growth & Advice, Early, Fundraising, Leadership, Q&A

Dear SaaStr: A Co-Founder is Asking for More Equity Post Fundraising. What Should I Do?

Dear SaaStr: A Co-Founder is Asking for More Equity Post Fundraising. What Should I Do? Listen. It usually means something is wrong. Or at least, off: If you got the equity splits right at first, usually, big issues don’t come up later. This may be a sign you need to fix things here. If your…
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Blog Posts, Exit Strategy, Q&A

There Are Exceptions. But Expect Your Valuation To Become Your Price Floor For An Acquisition.

Dear SaaStr: Does valuation play into how likely anyone would want to acquire the business from the founders? Absolutely. A lot. There is no question “too high” of a valuation can discourage an acquisition. Acquirers will generally assume they have to pay more than the last round price to buy you, and often 2x-3x more:…
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B2B SaaS Q&A - Tales of a Modern CEO with Atlassian and Trello (Video + Transcript) Blog Posts, Q&A

Dear SaaStr: What Are SaaS Billionaires Like?

Dear SaaStr: did you ever have a situation where you were talking to a person but that person turned out to be a billionaire? I’ve done OK, but I’ll never be a tech billionaire. However, I’ve met and worked with many (as crazy as that sounds to say “many”) in my start-up and SaaStr journey….
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Blog Posts, Career Growth & Advice, Early, Leadership, Q&A

Dear SaaStr: What Would Be The Single Most Important Advice You Would Give Other Entrepreneurs?

Dear SaaStr: What Would Be The Single Most Important Advice You Would Give Other Entrepreneurs? Quit today if you don’t want it bad enough. But … never quit if you truly do. … Now, by “quit” I don’t literally mean leave the keys on your desk and quit today. Not if you have investors, customers,…
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Other, Q&A

Dear SaaStr: Does a Big Exit Make You Happy?

Dear SaaStr: Does a Big Exit Make You Happy? Well here in the SF Bay Area … we live in a strange place. Folks I know with “infinite” money sort of fall into 3 buckets: Category 1: Still Building Stuff. For Whatever Reason. In their DNA. This is who they are. Oftentimes, they aren’t really…
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Blog Posts, Fundraising, Leadership, Q&A, Scale

Dear SaaStr: What Does “Old-School” Series A Funding Mean?

Dear SaaStr: What does “old-school” series A funding mean? Most likely: trying to buy 15-20%+ of a company, that is reasonably capital-efficient, and has at least product-market fit and some early traction, that hasn’t done endless seed rounds before the Series A, at a post-money valuation of < $30m-$40m The “traditional” or “old-school” venture business…
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Blog Posts, Early, Fundraising, Leadership, Q&A

Dear SaaStr: What Is The Average Time it Takes a VC to Make an Investment Decision?

Dear SaaStr: What Is The Average Time it Takes a VC to Make an Investment Decision? For hot seed and even Series A investments? 20 minutes into the first face-to-face meeting. The average VC basically makes the initial decision to tentatively invest very quickly — pending due diligence, confirming her theories are correct, and making…
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Blog Posts, Early, Fundraising, Leadership, Q&A

Dear SaaStr: What Kind of Background Checks Do VCs Do on Entrepreneurs They Fund?

Dear SaaStr: What Kind of Background Checks Do VCs Do on Entrepreneurs They Fund? It varies. Everyone does some background checks, or least they did outside of the Boom Times of late 2020 through late 2021. And some do very in-depth ones with lots of “off sheet” references (i.e., ones not provided by the CEO)….
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Blog Posts, Exit, Exit Strategy, Fundraising, Hiring, Human Resources, Q&A

Dear SaaStr: How Do Investors Feel About “Acquihires”?

Dear SaaStr: How Do Investors Feel About “Acquihires”? Back when I started investing, in 2013, VCs worked on getting acquihires for their struggling startups. A lot of energy was put in to find a “soft landing” for struggling investments running out of money, even if the returns might be nickels on the dollars. Today? VCs…
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Blog Posts, Exit, Exit Strategy, Fundraising, Leadership, Q&A

Dear SaaStr: Is It Normal for a Founder CEO to End Up With Just 10% Equity?

Dear SaaStr: Is It Normal for a Founder CEO to End Up With Just 10% Equity? Yes — if you are venture-backed. Roughly speaking, this is what generally will happen after 3 rounds of traditional venture capital. Expect it and plan for it. If the company sells 15–20% in each round, and 15–20% is reserved…
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Career Growth & Advice, Early, Exit Strategy, Leadership, Q&A

Dear SaaStr: What Should Happen When a Co-founder Wants to Quit?

Dear SaaStr: What Should Happen When a Co-founder Wants to Quit? This is one of the toughest situations to be in. First, figure out if it’s just anxiety. Starting something is hard. Getting to the first $1m in ARR is borderline impossible. If it’s “just” anxiety, and your co-founder is truly great at something —…
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