Expect Uncertainty | Ep 808
episodePreviously titled “Expect Uncertainty | Ep 826” — renamed by the publisher on Aug 2, 2026
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Why is entrepreneurship stressful due to uncertainty?
It's interesting how stressful entrepreneurship can be because of uncertainty. And so like right now, if we were to look back the last 15 years, we'd say something to the degree of, man, the stock market just went up 15 straight years. Like this was amazing. What a time to have invested, right? And Morgan Housel wrote a little blog about this. And so I thought it was so interesting. He said,
What lessons can we learn from past market dips?
wait a second, that's not true. Like we had a 20% dip in 2011. We had a dip in 2016. 2020 obviously happened in that period of time. We had wars that didn't end. And so all of these things were kind of happening. And I say this not as a political statement, but more so that everything seems better in retrospect because there is no uncertainty. We know how the story ends. And so I think in some ways it's like, that can give a certainty that our current situation, despite the fact that it feels terrible, it always resolves or we die. And so like, if you die, you don't have to worry about it. And if it resolves, you don't have to worry about it.
How can we frame uncertainty in business?
And so that's kind of been a helpful framework for me because I think a lot of the stuff of what makes entrepreneurship difficult isn't really the tactics. Like learning the things that you have to do, those are just kind of knowledge deficiencies and we have to learn those for sure. But I think everyone here would agree that that's not what makes your job every day hard.
What makes entrepreneurship challenging beyond tactics?
Learning how to set up a landing page, maybe you don't know how to do it, but it's not gonna kill you to learn it. It's when your manager leaves and takes half of your team and all of a sudden your payment processor shuts down and you've got leads that are coming in but you can't make payroll. That's the stuff that makes it really stressful. The actual tactics of business are relatively straightforward. And so I say this just as a reminder almost to myself that It's, you know, the future is likely going to be better. The past is not as good as we remember it to be. And so I think that's relatively a hopeful message for entrepreneurs. The second thing, and so this is a little bit more strategic, is...
How do we effectively prioritize resources in business?
I do a lot of quarterly and annual planning with the portfolio companies. I have gone through that motion a lot of times. I've distilled this down into a little mini framework that's worked really well for me because you go through 10 or 20 or 50 or 100 of them and you're like, okay, I think I know how this is going to go. I define strategy as prioritization of resources, and if I wanted a longer definition, it'd be prioritization of limited resources against unlimited options. Fundamentally, the people who move fastest, or the businesses who move fastest, are the people who are the best allocators of those resources to the things that get the best returns. For many of you here, you'll have this big list of things that you're thinking about doing. And the objective of this Q&A session, hopefully not just necessarily for your question, but for someone else's question, is that when you go home or when you fly back, you're going to have all your notes on one side, and you're probably going to have a fresh piece of paper or document on another screen.
And you're going to be like, OK, I have nine pages of notes. What am I actually going to do? And then you're going to write three to five things on that other page. I just want to make sure we get those three to five things right because that is what makes this worth it or not. So I break this into what, how, and who.
What key objectives should drive our business strategies?
And although this seems really simplistic, I've also found that simple frameworks are the ones you actually end up coming back to and using. And so fundamentally, every single what that you got from today and yesterday should ladder up to one of three objectives. So number one is it should increase the number of customers that we get, so number of new customers, number of sales. It should increase the lifetime gross profit per customer, or it should decrease risk. So fundamentally, these are the things that make a company more money. This is what makes a company valuable. So if we are going to consistently sell more customers, and they're going to be worth more in the future, and we believe that that future is incredibly certain, that is very valuable business.
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Chapters
8 chapters
1
Why is entrepreneurship stressful due to uncertainty?
0:00–0:24
2
What lessons can we learn from past market dips?
0:24–1:07
3
How can we frame uncertainty in business?
1:07–1:24
4
What makes entrepreneurship challenging beyond tactics?
1:24–2:04
5
How do we effectively prioritize resources in business?
2:04–3:22
6
What key objectives should drive our business strategies?
3:22–4:03
7
How can we determine the best business initiatives?
4:03–6:09
8
What is the best approach for acquiring more customers?
6:09–13:53