SaaStr

MARCH 26, 2024

Since then, I’ve made some pretty good other investments as well. The top reasons an investment has turned out to be a Zero: #1. The post The Investments Where I’m Going to Lose All My Money appeared first on SaaStr. cash Second was Algolia leading U.S. But also, I made some that … weren’t.

Investment 328

Investment Scale Churn SaaS 328

SaaStr

MAY 3, 2025

Dear SaaStr: Is it True VCs Don’t Like to Invest Where Founders’ Equity is Fully Vested? Yes, it’s true but … #1. VCs Are Less Rigid Here Than They Used To Be If a deal is hot and you have multiple offers, VCs won’t push as hard here as in the past.

Investment 137

Investment Management Leadership 137

Sales Hacker

NOVEMBER 29, 2024

GTMfund’s 3 Areas of Focus for Investing Thanksgiving weekend is always a period of reflection and gratitude. Reflection across go-to-market trends, but also on the investment front (not to mention community !). A common misconception is that the name is representative of the type of software we invest in.

Investment 113

Investment Technical Review Development Team Review Scale 113

SaaStr

SEPTEMBER 2, 2024

Dear SaaStr: Should You Always Ask a Co-founder to Invest Their Own Money? And many times even a small investment will be very stressful for some co-founders. However, whoever contributes cash should usually either be repaid, at least partially, or get extra equity for that investment. I made 12x on that investment.

Investment 312

Investment Startup Leadership 312

SaaStr

SEPTEMBER 20, 2024

Dear SaaStr: Do angel investors or seed venture capitalists normally ask for detailed budgets including cash flow analysis before investing, even though most of the numbers will be pure speculation? The post Do Angel Investors and Seed VCs Ask for Detailed Budgets Before Investing? When it is, you can learn a lot.

Investment 308

Investment Sales Hiring Business Model Sales 308

SaaStr

OCTOBER 30, 2024

We’re obviously written up a lot about Fundraising and Investing here on SaaStr.com, but time and time again, SaaStr CEO and Founder Jason Lemkin has seen so many Founders sign a bad term sheet based on gut instinct, VC celebrity or vibes, and while that may be fine, it’s not enough.

Venture Capital 316

Venture Capital Software Review Investment Startup 316

SaaStr

OCTOBER 29, 2024

Most Smaller VC Funds ($100m or smaller fund) would like to own 10% or more after a Seed or Pre-Seed Investment , but typically model around 7% average ownership. If it’s not a core investment, VC funds may be more flexible. But these exceptions to ownership targets make these investments non-core.

Investment 288

Investment Pricing Engagement Leadership 288

SaaStr

JULY 9, 2024

Those rare investments that return enough money to the VC fund to pay off at least 1x the total fund size. And you can see VCs are often pretty careful to make sure structurally, any given investment can do it. Investing in the #3 or #4 in a space? It’s not what anyone hoped when they invested. A 1% stake?

Investment 307

Investment Venture Capital Social Media Startup 307

SaaStr

MAY 18, 2024

Dear SaaStr: Have You Ever Made a Very Risky Investment That Paid Off Big Time? More of the story here: The post Dear SaaStr: Have You Ever Made a Very Risky Investment That Paid Off Big Time? In my first start-up, the VCs pulled our term sheet between signing and closing. But sometimes … you just do it. appeared first on SaaStr.

Investment 306

Investment Leadership 306

SaaStr

DECEMBER 23, 2024

Share everything anyone would want to know to invest in you. But unless you are raising from folks that truly invest pre-revenue, investors are going to want to see 3 strong months of growth in a row. If nothing else, point out an existing investment or two theyve made that is somewhat similar to yours. # Share it all.

Venture Capital 279

Venture Capital Investment AI Metrics 279

SaaStr

DECEMBER 20, 2024

Having led sales teams of 500+ at BILL and 800+ at HubSpot, Michelle has unique insights into what makes great frontline managers and why investing in them is crucial for sustainable growth. “At HubSpot, I had over 100 frontline sales managers reporting to me. ” The bottom line?

Sales Hiring 263

Sales Hiring Scale Underperforming Technical Team Sales 263

SaaStr

MAY 16, 2025

First, if youre not sure they want to invest they probably dont want to. The One Question To Ask At The End of Every VC Pitch: What Are The Odds You Would Invest? Just ask what are the odds theyd want to invest, based on what they know now. And its 100% OK to ask. This can lead to hesitation or misaligned expectations.

Investment 178

Investment Startup Communication Engagement 178

SaaStr

MAY 5, 2025

This reduces the perceived risk of adopting a new solution, especially if theyre replacing an existing system or investing significant resources. If key stakeholders or end-users see the value during the pilot, its much easier for the client to justify the investment to their leadership team. Risk reduction is key.

Enterprise 245

Enterprise Leadership Investment Metrics 245

SaaStr

NOVEMBER 17, 2024

3 Came from the Investment Bank They Hired. In my experience, hiring an investment bank to help you in any acquisition > $100m or so is critical. Hit $20m ARR, growing 30%-40%, with little to no burn, and PE firms will begin to find you. #2. They Ran a Crisp, Tight Process And Got 4 Offers to Buy Them.

Sales Hiring 299

Sales Hiring Banking Sales SaaS 299

SaaStr

NOVEMBER 2, 2024

Having been through 4 acquisitions in different forms (founder, exec, etc), it’s a lot like a venture capital investment. A ton of time is invested negotiating price, and then way, way too much time on inconsequential legal terms, and then … it closes. Usually, there isn’t actually a ton of time to really get to know each other first.

Venture Capital 264

Venture Capital Acquisition Investment Technology 264

SaaStr

NOVEMBER 13, 2024

But it’s clear that it’s still in the investing phase, and increasing spend in sales & marketing. Outside of a pre-IPO phase, Klaviyo has been cash-flow positive or close for most of its history. Today, it’s steadily driving its margins up, now up to 14% non-GAAP operating margins.

Scale 306

Scale SMB Scaling Enterprise 306

SaaStr

MARCH 16, 2025

Follow the Pilot-Repeat-Enlarge Methodology Pilot : Start small with minimal investment. Use a Hypothesis-Driven Approach For each campaign, establish: A clear hypothesis Time limits Budget constraints Minimum success criteria Most importantly, define what “success” looks like before you start.

Scale 246

Scale Sales Hiring Scaling Marketing 246

SaaStr

FEBRUARY 11, 2025

The winner(s) will receive funding from the Mayfield AI Garage, who are at the forefront of investing in cutting-edge tools at the intersection of SaaS and AI. You could win $500K – $5M in funding from Mayfield AI Garage!! That’s right. This is epic opportunity to showcase your AI Startup. Win $500k – up to $5M in funding.

AI 305

AI Startup Innovation Investment 305

SaaStr

OCTOBER 25, 2024

It’s now falling to 150 because 81% percent of the dollars invested in venture capital at the height of the boom came from non-traditional venture capital firms which are all very likely to leave investing. US venture funding went from 8 to 300 over 15 years.

Venture Capital 333

Venture Capital Marketing AI SaaS 333

SaaStr

DECEMBER 26, 2024

I havent done that, but Ive done handshake deals in one day in maybe 50% of my investments (i.e, Not literally months to do the homework that doesnt take long but sometimes months to see enough progress for the investment to make sense to me, to connect enough dots. Yes, term sheets get done in one day.

Investment 246

Investment Pricing Leadership 246

SaaStr

OCTOBER 22, 2024

In my ecosystem, most do another start-up, invest, or do something related: For some, it’s ego. Dear SaaStr: Why Do CEOs Keep Working After Making a Lot of Money? It’s a great question. Some don’t keep working. Some are happily retired. But not most in my ecosystem. For some, they get bored. For some, it’s to go even bigger.

Investment 277

Investment 277

SaaStr

DECEMBER 30, 2024

There are really three modes from a VC perspective during a fundraising pitch: You Almost immediately want to do the investment. This is 80%+ of the investments Ive done. Almost all my investments at SaaStr Fund , Ive told the founders before the meetings end that Im in if everything theyve said checks out. The Likely Nos.

Startup 264

Startup CTO Investment Marketing 264

SaaStr

OCTOBER 31, 2024

Basically I only invest in first-timers. First-timers do just as well, if not better, than second-timers. And they are much more capital-efficient. Not always, but often. And they lack the biases of second-timers. The post 6 Of The Most Common Mistakes I See First Time SaaS Founders Make appeared first on SaaStr.

Scale 312

Scale SaaS Social Media Business Model 312

SaaStr

NOVEMBER 20, 2024

Don’t underestimate the investments you need to make here to be compelling to your customers. Another big investment during rapid growth is digital moments. You want to invest time and energy here so that partners are ready to talk to customers. Then, package that up into a narrative that makes sense.

Scale 264

Scale AI Scaling Marketing 264

SaaStr

NOVEMBER 19, 2024

But I’d say 90% of SaaS companies I work with and have invested in don’t get these basics right for a long, long time. Even if churn isn’t that high today — it likely will be later. I see many SaaS start-ups with mediocre retention with … mediocre NPS (20-30). Yes, a lot of this sounds basic. Not for real. NPS is A Great Core Metric.

Churn 275

Churn Retention Scale Investment 275

SaaStr

JANUARY 14, 2025

Their “sense” of what things cost is often just way too low once they start to invest the first round of VC capital they raise. And how much that dramatically drives up the burn rate and cost of doing business. Dramatically. This especially bites founders that get pretty far bootstrapping.

Startup 279

Startup Finance Engineering Investment 279

SaaStr

MARCH 17, 2025

Massive investments, at massive valuations, into the biggest leaders of AI. Now there’s a lot going on here and part of the rush in 2024 and 2025 is that more capital is coming into VC again. But it still shows where the energy and momentum are. At a scale we haven’t seen before.

Venture Capital 315

Venture Capital AI Scaling Investment 315

Clouded Judgement

NOVEMBER 18, 2024

The purpose of the detailed information is to help investors (both institutional and retail) make informed investment decisions. The document contains a plethora of information on the company including a general overview, up to date financials, risk factors to the business, cap table highlights and much more.

Benchmarks 299

Benchmarks Payments Payment Services SaaS Payments 299

SaaStr

MAY 10, 2025

Invest in Relationships Customer success isnt just about metricsits about people. Dont wait until youre at $5M or later to invest in customer success. And be very careful if you have Customer Success report to a CRO or to sales. Be careful here. Build strong, human connections with your customers — for real. Start Early.

Sales Hiring 235

Sales Hiring Customer Success Scale Retention 235

SaaStr

DECEMBER 27, 2024

The losses arent equal, and you can mitigate them by not making further investments. Why $300 Billion? Roughly, VCs model losing money on about 40% of their deals, but only 20% overall. So if roughly weve raised $300B a year over the past 5 years, more or less then 20% of that total would be $300 Billion.

Startup 246

Startup Investment Data 246