relentlessly resourceful
A few days ago, I was reading Paul Graham’s A Fundraising Survival Guide. I originally opened it because I wanted to understand how founders should think about raising money. The essay was interesting, but there was one paragraph that completely distracted me from fundraising haha
Graham was talking about independence. He argued that investors tend to like founders who look like they will succeed with or without them. Then he used Sam Altman as an example:
“You could parachute him into an island full of cannibals and come back in 5 years and he’d be the king.”
Bro 😭
That is probably one of the craziest compliments I have ever read.
Some time before this, I had read another essay by Graham called Relentlessly Resourceful. In that one, he was trying to describe the quality that distinguishes really good startup founders, and eventually landed on those two words: relentlessly resourceful.
And you know what? When I read that part about Sam in A Fundraising Survival Guide, it immediately reminded me of that other essay.
I remember thinking, this is probably what Graham meant, right?
Take someone out of their usual environment, remove the obvious resources they normally rely on, and somehow they still find a way to make things work.
That Sam example made the idea much more concrete for me. I could finally picture the kind of person Graham was talking about.
But then I started wondering about something else: how do you actually become that kind of person?
Not just understand what relentlessly resourceful means, but actually build that quality into the way you think and act when things go wrong.
How do I make myself keep looking for another way instead of getting stuck on the first one? How do I get better at figuring things out when I do not have the resources, connections, or answers yet?
That is what I actually want to figure out.
In Graham’s essay, the opposite of relentlessly resourceful is hapless. Not simply unlucky, but someone who mostly lets circumstances decide what happens next.
Graham uses a running back in American football as an analogy. I barely know how American football works either lol, but the point is simple: you know where you want to go, but you cannot know the exact route beforehand. Things get in the way, openings disappear, and you have to keep adjusting while still moving toward the same destination.
I think this is the part I like most about the phrase. Being relentless alone is not enough. You can keep pushing forever and still get nowhere if you are just repeating something that clearly does not work.
The resourceful part is knowing when to change the way you are doing things without giving up on what you are trying to achieve.
So the way I understand it is pretty simple: be stubborn about the outcome, but flexible about the path.
One of the earliest examples comes from Loopt, Sam Altman’s first startup. Back then, Loopt could not simply publish an app and instantly reach millions of people. To make its location-sharing product work at scale, it needed access to the mobile carriers themselves.
According to Sam’s own account, one night around 11 PM, Loopt got some pretty terrible news: Boost Mobile, one of their first major potential customers, had decided to go with a much larger and better-funded competitor instead. Sam was 20 years old.
At 6 AM the next morning, he was on a flight to Orange County.
He went straight to Boost’s office, sat in the lobby, and waited for the person responsible for the deal to arrive. The decision had supposedly already been made, but Sam convinced him to look at Loopt’s demo anyway. His team had spent the previous days figuring out which features mattered most to Boost, so they tailored the demo around them.
Sam later said he ended up hanging around for about two weeks.
Eventually, Loopt got the deal. The service launched with Boost in 2006, expanded to Sprint and Verizon over the next couple of years, and by the end of 2008 was available across the major US carriers.
Years later, when Sam was asked how a 20-year-old managed to build those kinds of relationships, his answer was surprisingly simple:
“You just sort of show up.”
Which is a very casual way to describe getting on a 6 AM flight, waiting in someone’s lobby, and refusing to treat a supposedly final decision as final 🤣
But I guess that was exactly his point. Boost thought the conversation was over. Sam apparently did not lol
Airbnb’s founders had an even stranger story of their own. Before the company became successful, Brian Chesky and Joe Gebbia were struggling to raise funding and had accumulated a significant amount of credit card debt. They needed money to keep Airbnb alive, but investors were still not particularly interested in the idea.
During the 2008 US presidential election, they noticed how much attention was focused on Barack Obama and John McCain. They did not have investor money, but they still had their design skills, a major cultural moment they could use, and the ability to create something people might actually buy. So they designed two limited-edition cereal boxes called Obama O’s and Cap’n McCain’s, bought cereal in bulk, assembled the boxes themselves, and sold them for $40 each. For a while, the founders of a housing startup were spending their time packaging and selling breakfast cereal lol.
As strange as it sounds, the idea worked. They made around $30,000 from the cereal, giving them some breathing room while they were still struggling to raise money.
All of this happened before they joined Y Combinator. When they later applied, they brought the cereal boxes to their interview and explained how they had used them to help fund the company. Paul Graham later recalled that the story affected how he viewed the founders. He was still uncertain about the Airbnb idea, but the cereal showed that Brian and Joe were willing to work with whatever resources they had instead of waiting for the resources they wished they had.
The cereal obviously did not solve all of Airbnb’s problems. But it kept them going, and it showed YC something that was probably much harder to communicate in a pitch: when they did not have the resources they wanted, they were willing to work with whatever they had.
Looking at Sam and Airbnb, I think the pattern is pretty simple. They knew what they needed, but they were not too attached to one particular way of getting it. Sam needed access, and even after the deal was supposedly gone, he kept trying to get back into the conversation. Airbnb needed money, and when investors were not interested, its founders somehow ended up selling cereal.
I think that is the habit we have to build. When something does not work, figure out what we are actually trying to achieve, ask what else could get us there, and -- probably the most important part -- actually go do something about it.
We are going to get some of those attempts wrong. That is fine. Now we know something we did not know before, and we can try again. Maybe being relentlessly resourceful is really just getting very good at doing that over and over.
Sources & Further Reading
Paul Graham -- Relentlessly Resourceful
Paul Graham -- A Fundraising Survival Guide
Sam Altman -- Hacker News AMA -- the Loopt / Boost Mobile story
Y Combinator -- Sam Altman on Founders and the Fear of Rejection -- including “you just sort of show up”
Paul Graham -- What We Look for in Founders -- including the Airbnb cereal story