The Ledger

Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.

clear all ✕

why aren't all 11 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Insight
Osterman: Acquisition buyers wait for competing offers or firm deadlines
“There's also a point when you're in an acquisition process where you have a bunch of people interested, but no one's going to jump until someone else jumps and like gives you an offer or like there's some deadline.”
Harris Osterman Oct 16, 2024 ▶ 11:23 How to Build SaaS for an Industry No One Knows About (Except Your Customers)
Insight
Osterman: Working capital requirements can secretly gut your acquisition proceeds
“Working capital requirements can really screw you over, you know, cut your deal.”
Harris Osterman Oct 16, 2024 ▶ 13:29 How to Build SaaS for an Industry No One Knows About (Except Your Customers)
Insight
Osterman: Buyers hold all negotiating leverage after an LOI is signed
“Once you sign the LOI now the buyer has all the power, and, like, if they back out, now you have to go back to the other buyers.”
Harris Osterman Oct 16, 2024 ▶ 15:45 How to Build SaaS for an Industry No One Knows About (Except Your Customers)
Disclosure
Osterman rejected higher acquisition offers to avoid post-sale earnout requirements
“There were offers that would have earned me a lot more money, but I'm not going to be running the business anymore. So I don't really want to do that.”
Harris Osterman Oct 16, 2024 ▶ 16:55 How to Build SaaS for an Industry No One Knows About (Except Your Customers)
Insight
Osterman: Three consecutive profitable years guarantees buyer confidence in SaaS
“If you run a business, and it has at least three consecutive prior years of profit, and like, let's say six figures of profit, like a very small amount that's what buyers want. So, like, there are a lot of companies that have had a lot of profit, but they're p…”
Harris Osterman Oct 16, 2024 ▶ 17:34 How to Build SaaS for an Industry No One Knows About (Except Your Customers)
Assertion Not checkable as stated
Osterman: Talk Hiring evaluated seven acquisition offers from varied buyers
“We had seven different offers that we were considering but it was tough to vet all of them, and, like, some of them were public companies, some of them were private startups, some of them were, like, individuals, some of them were search funds”
Harris Osterman Oct 16, 2024 ▶ 13:03 How to Build SaaS for an Industry No One Knows About (Except Your Customers)
Insight
Osterman: Mitigating revenue and distribution concentration is essential when selling a business
“Buyers are always, not always, but generally wary about if you have certain, like, a certain percentage of your customers, or a certain percentage of your revenue comes from a small percentage of customers. It's tough to avoid that, though, as a company. Like,…”
Harris Osterman Oct 16, 2024 ▶ 19:04 How to Build SaaS for an Industry No One Knows About (Except Your Customers)
What-if
Osterman: Commingling product lines prevents buyers from securing SBA acquisition loans
“The problem for our business was that we had multiple product lines under the same corporate entity, and therefore we were filing taxes every year as like a combination of all of our Product lines. And then, like, the SBA always wants to see the tax filings, a…”
Harris Osterman Oct 16, 2024 ▶ 20:46 How to Build SaaS for an Industry No One Knows About (Except Your Customers)
Disclosure
Osterman traded free beta access for mandatory weekly feedback meetings
“Like they were one of our probably 10 or 15 design partners. So we started off giving away for free as like a free beta. And as a condition of using this thing for free, you had to meet with me. Every week, so I got a lot of feedback.”
Harris Osterman Oct 16, 2024 ▶ 4:11 How to Build SaaS for an Industry No One Knows About (Except Your Customers)
Opinion
Osterman: Career readiness organizations are an underserved and viable SaaS niche
“We really focused on the niche of career readiness organizations because they were very underserved as a market and a good, you know, business to build off of.”
Harris Osterman Oct 16, 2024 ▶ 7:11 How to Build SaaS for an Industry No One Knows About (Except Your Customers)
Disclosure
Osterman previously tried selling Talk Hiring but overpriced it
“A few years ago, I considered selling the business because I was considering raising money for the job searching tool and thought, like, I can't be running two product lines at the same time, so I priced it way too high, did not get enough interest”
Harris Osterman Oct 16, 2024 ▶ 7:30 How to Build SaaS for an Industry No One Knows About (Except Your Customers)
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