The path of least assumptions
Brief essays from the trenches / Dispelling startup myths
This is a newsletter about building a software company, written from the trenches of building one.
I write brief essays to reflect... and to counter all the startup myths and “hacks” peddled by influencers looking to make a quick buck.
This week’s essay tl;dr:
“What is the path to solving this that requires the least number of things to be true?”
Sell to buyers
A good friend is releasing a great business book this year.
He’s finished the editing, branding, writing, and rewriting. Now he just has to sell books.
Here’s the funny thing about selling business books: It’s more like selling software than selling mass market books. You go to B2B buyers and pitch them on buying lots of copies and speaking engagements.
The challenge with a business book - just like B2B software - is that there are a lot of people who could possibly be buyers. In his case, his buyers could be:
Business unit leaders
Various HR departments
Various university departments
Various nonprofit departments
He could sell to different industries, use different messaging,
But he has limited time and resources. What should he do?
The “correct” answer is: He should experiment. (Duh.)
The problem is that there are so many variables and so little time to find signal, he can’t infinitely experiment.
So he’s approaching this by asking himself: Who are the 2-3 groups most likely to be able and willing to make a quick decision on a purchase?
In other words: Prioritize selling to the people who are likely to buy, and buy quickly.
Deprioritize selling to roles that would likely take 10 meetings over 10 weeks with 10 different decision-makers to get approval to ask external decision-makers to finance a purchase order for only 10 copies…
In reflecting on his direction, there is a broader principle at play:
Pursue the path of least assumptions
A lot of my startup friends pursue go-to-market channels and customers that require a lot of things to wind up working in their favor. They go the path of many assumptions.
We should find the directions that require LESS things to work in our favor initially. Here are a few examples:
Go-To-Market: SEO vs. Cold Outreach
Founders love SEO. But SEO requires you to get a lot of things right, takes a long time to get right, and gives you limited feedback until it’s working:
You have to rank on Google for certain search terms (not easy)
Once you rank on Google for those search terms, you have to convert website visitors to customers (really freakin’ hard)
The alternative is cold outreach, where you email, call, and LinkedIn message people who should be your customer and, if your message is compelling, you get conversations started.
Cold outreach requires less things working in your favor initially - and most of the things that need to work in your favor are within your control.
(Don’t even get me started on “virality” as a growth channel.)
Customers: Enterprise vs. mid-market
Enterprise customers are willing to pay a LOT more, but they also take forever to make decisions and have a lot of decision-making variables that are outside your control. Enterprise buyers are also “nicer” and won’t tell you your product is dumb.
Mid-market companies can often make a quick decision - whether that’s to tell you to screw off OR to buy.
Play games you can win.
When deciding among multiple paths, consider the path that requires fewer things to be true. Even better if the things that must be true are concrete and in your control, versus abstract (“customers have this pain point”) and out of your control (“they’ll tell all their friends about it”).
In my future, I’ll prioritize:
Business ideas that have clear paths to clear customers who can make quick decisions (start mid-market with cold outreach and get money up-front)
Narrower initial products with clearer differentiators that require fewer features “working right” to provide value. (Avoid marketplaces, multi-stakeholder products, ambiguous value props)
Asking myself the question: “Which of these options requires less to be true?”
I can set up the game however I want, so I’m going to set it up to win. Which means getting real, really fast.
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