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Blog Posts, Early, Fundraising, Q&A
Dear SaaStr: What’s a Big Check for an Investor?
Q: What’s considered a large amount of money for an investor? A rough answer is more than 1.5%-2% of their fund size is a “lot of money” for most…
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Blog Posts, Early, Q&A
Dear SaaStr: How Old is “Too Old” To Start a SaaS Startup?
Q: How old is too old to start a startup? IMHE it’s about a state of mind.. Let me try to add some practical answers: 1. First, you need to give…
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Blog Posts, Early, Featured Q&A, Product, Q&A, SaaS Product Pricing
The 3 Types of Day 1 Pricing: Low End of Normal. Identical. And Anchor High.
Q: As an entrepreneur starting out, is it better to overprice your product or underprice it? I remember years ago I was at an event with the CEO of a…
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Blog Posts, Hiring, Q&A
Dear SaaStr: Do My VP of Eng and My VP of Product Have to Be Technically Excellent?
Dear SaaStr: Do My VP of Eng and My VP of Product Have to Be Technically Excellent? This has been pretty much my experience A Great VP of Engineering must either:…
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Blog Posts, Q&A, SaaS Product Pricing
Dear SaaStr: Does Freemium Always Work?
Q: Dear SaaStr: Does Freemium Always Work? No. Freemium and PLG models don’t always work. And sometimes, they only work partially. For Freemium to work, you need at least 2…
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Blog Posts, Fundraising, Q&A
10 of the Top Mistakes I’ve Made in Venture Investing
Q: What are the most common mistakes people do while investing? My top mistakes, in venture investing, at least: Investing when I didn’t 100% believe in the CEO. No matter…
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Blog Posts, Q&A
Dear SaaStr: Will Peloton Be Filing Bankruptcy or Selling Within 2022?
Dear SaaStr: Will Peloton Be Filing Bankruptcy or Selling Within 2022? Bankruptcy: No. Almost Run Out of Money: Probably. They are already running out now. Sell: 50/50 chance … Peloton…
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Blog Posts, Q&A, Scale
Dear SaaStr: Do You Think Palantir Will Be a Strong Company In the Near Future?
Dear SaaStr: Do You Think Palantir Will Be a Strong Company In the Near Future? Palantir will be a strong company for at least a decade. Why? It’s Just Math….
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Fundraising, Q&A
Dear SaaStr: How Much Money Do You Need to Be An Angel Investor?
Dear SaaStr: How Much Money Do You Need to Be An Angel Investor? You can certainly start with a few small checks — to learn. As long as they are…
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Blog Posts, Q&A
Dear SaaStr: How Fast Should your Monthly Growth Be from $0 to $1M ARR?
Dear SaaStr: How Fast Should your Monthly Growth Be from $0 to $1M ARR? I can tell you after 30+ SaaS investments, including 5 unicorns … it doesn’t really matter…
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Blog Posts, Product, Q&A, SaaS Product Pricing
Anchoring High in Pricing Really Works. But Only If You Do It Really Well.
Q: If I produce a better product than my competitors, but charge a little more, how would I go about selling it (to new customers and my competitors customers)? “Anchoring…
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Blog Posts, Fundraising, Q&A
Why A 4-5x Return On an Investment Isn’t “Good Enough” For Earlier-Stage VCs
Q: Will VCs who invested in my startup be happy to exit with a 4-5x return after 4.5 years? It’s hard to say. On average, VCs are looking for the…
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Blog Posts, Career Growth & Advice, Growth, Leadership, Marketing, Q&A, Sales
Dear SaaStr: How Hard is it for SDRs to Move into AE roles?
Q: Dear SaaStr: How Hard is it for SDRs to Move into AE roles? It’s a well-proven path. If you want to get into SaaS sales, start at SDR and…
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Blog Posts, Q&A
Dear SaaStr: Do Customer Testimonials Really Work? How?
Q: Do customer testimonials work? How? They work — if done right. And they are incredibly important. We spend so much time marketing and selling to customers. And building stuff…
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Blog Posts, Growth, Q&A
The Only 2 Things That Really Motivate a Salesteam
Culture matters. Growth matters. Mission matters. They all matter. You have to do this. And that may be enough for most of your early employees. They may even be OK…
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Blog Posts, Q&A
Dear SaaStr: What Can You Do Once You’ve Been Offered a Term Sheet to Make the Deal Competitive?
Q: What can you do once you’ve been offered a term sheet to make the deal competitive? It’s not that complicated. You generally have one option: let everyone else you…
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Blog Posts, Product, Q&A
9 Things Your New Head of Product Should Do in Their First 30 Days
Q: Where should a new product owner (PO) focus in their first 30 days? My strong advice is speak with data. And that may mean at first — not speaking too…
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Blog Posts, Q&A, Sales
Dear SaaStr: How Much Outbound Revenue Should a SDR/BDR be Generating at a Mid-stage Enterprise SaaS Startup?
Q: Dear SaaStr: How Much Outbound Revenue Should a SDR/BDR be Generating at a Mid-stage Enterprise SaaS Startup? A high performing SDR at a mid-sized deal size will: Set up…
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Blog Posts, Early, Q&A
Dear SaaStr: In the Early Days, What Does a Business Co-founder Do While the Technical Co-founders are Programming?
Q: What does a business co-founder do while the technical co-founders are programming? Here’s what I did: Recruited a bunch of the rest of the team. Raised the Series A….
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Blog Posts, Career Growth & Advice, Exit, Exit Strategy, Leadership, Q&A
Dear SaaStr: When Should You Sell Your Company?
I was with the CEO of a $XB+ SaaS CEO a little while back He was acquiring a leanly-funded startup. The founder owned so much, he would make more than…
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Blog Posts, Q&A
Dear SaaStr: What is the Best Way to Deal with Long Sales Cycles?
Dear SaaStr: What is the Best Way to Deal with Long Sales Cycles? First, shorten them up a bit. Don’t fear paid pilots, opt-outs after 60-90 days, and/or smaller deployments….
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Blog Posts, Early, Q&A
Dear SaaStr: How Much Do I Pay My First Sales Rep?
Dear SaaStr: How Much Do I Pay My First Sales Rep? Three ways to simplify the answer here, especially in the early days: In the end, in base salary AND…
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Blog Posts, Early, Q&A
Dear SaaStr: Is it Bad to Leave a Failing Startup?
Dear SaaStr: Is it Bad to Leave a Failing Startup? It can be a tough situation. If you’re a critical resource and leave a struggling startup — would that increase…
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Blog Posts, Early, Q&A
The 8 Biggest Mistakes First Time Founders Make After $50K MRR Or So
Q: What are the biggest mistakes first time founders make after $50K MRR in SaaS? A partial list of the ones I see all the time (and mistakes I made…
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Blog Posts, Customer Success, Growth, Q&A, SaaS Product Pricing, Sales
Dear SaaStr: How Do You Change the Price of Your SaaS Product Without Upsetting Existing Customers?
Raise prices on existing customers,Doesn’t help if you are growing quickly. Just makes them unhappy. Raise prices on new customers,Forces you to deliver more value. Often makes everyone more happy….
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Popular Q&A
The 3 Types of Day 1 Pricing: Low End of Normal. Identical. And Anchor High.
Q: As an entrepreneur starting out, is it better to overprice your product or underprice it? I remember years ago I was at an event with the CEO of a SaaS leader. And I asked him how he came up with their freemium pricing model. A data science team? A/B Testing? "No....
7+ Tips On How To Build Your First Sales Team
Q: How do you structure a sales team when you’ve got zero experience doing sales? Well, first go get some experience with sales. 🙂 At least, close the first 10 customers yourself. If you don’t, you’ll never have any idea how to do it. And the odds your first rep...
Why SMB Reps Struggle in the Enterprise. And Vice-Versa.
Q: How is low/mid-ticket sales different from enterprise sales? They are very, very different. If I had to boil down how to filter potential sales professionals based on just 1 controlling criterion, it would be deal size. Enterprise sales: Reps often hunt many of...
The Top 50 SaaStr Answers on Quora in 2020
It's been a fun experience being on Quora for ... a decade 🙂 We've crossed 60,000,000 views of our answers there, so let's take a look at the Top 50 most viewed SaaStr Answers on Quora in 2020: Why do many startup owners sell...
7+ Tips On How To Build Your First Sales Team
Q: How do you structure a sales team when you’ve got zero experience doing sales? Well, first go get some experience with sales. 🙂 At least, close the first 10 customers yourself. If you don’t, you’ll never have any idea how to do it. And the odds your first rep...
Can an Entrepreneur Back Out of a Signed Term Sheet Without Damaging Their Reputation?
Can an entrepreneur back out of a signed term sheet without damaging his/her reputation? I’m going to say Yes, probably. There is a lot of drama around broken term sheets. Mostly around VCs backing out, not founders. But here’s the thing — term sheet are term sheets....
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