I co-wrote this new essay with Charlie Songhurst about when founders need chaos vs conscientiousness. Charlie is on Meta's board and he's a prolific angel investor. Here's [[Chris Barber|about me]] and [my twitter](https://x.com/chrisbarber). *By Chris Barber and Charlie Songhurst* This is advice for founders to maximize their expected value. Startups go through phase transitions and the traits required to succeed change at each stage. In most markets, the early stages require chaos -- think the highly creative artist, who has notes and notes full of ideas, builds dozens or hundreds of side projects, and explores the territory thoroughly. The scaling phases require more conscientiousness -- think the disciplined to-do list machine who can remain highly focused on one thing for years on end, is impossible to distract, can sit in meetings for twelve hours a day, and plans their agenda weeks in advance. Founders can increase their odds of success by being aware of their dominant trait and ways to mitigate their weak trait. ![[chaos-to-conscientiousness.png]] **The early exploration phase** The early exploration phase is about finding your global maximum. The high chaos founder doesn’t need much help here. They’ll naturally explore broadly. The high conscientiousness founder either needs to get lucky, or they’d do well to surround themselves with a bunch of high chaos types, so that they can explore via osmosis. If you’re a conscientious type, pay attention to what your high chaos friends are finding interesting, especially if those things don’t seem like serious fields yet. One error that high conscientiousness founders make is not exploring broadly enough. They might try one or two highly polished projects, rather than a large number of low-polish projects. Low-polish projects probably won’t find PMF, but they can show signs of spark and indicate where high effort is worth it.  **The building to PMF phase** This is about spending as much time with customers as possible and getting high retention and high engagement. The ideal is to have high conscientiousness and high chaos. This is tricky. Your options: 1. Co-founder pairing. Conscientious founder + chaotic founder. 2. Solo founder with both traits. Rare but happens. 3. Go with your strength and accept the gap. Likely to take longer to iterate to PMF. 4. Pick an industry where your weakness doesn’t matter. B2B SaaS doesn’t require high chaos at any stage. Network effect businesses are the inverse of SaaS: if you can muster enough conscientiousness to get it off the ground, then you can survive on chaos, because the network effect hides weaknesses. 5. Attempt to patch your weakness. The high chaos founder that goes to founder focus meetings, does body doubling, takes appropriate and legally prescribed medication, joins an accelerator or hacker house as a motivation forcing function, or assembles a group of their friends to serve as accountability. The high conscientiousness founder that surrounds themselves with high chaos types and pulls together a group of their most creative friends to give them ideas when they’re stuck. One error that high conscientiousness founders make is to suppress chaos too early before PMF. They end up with a good business and miss the great one that was adjacent. They systematize things too early, prematurely moving from explore to exploit. One error that high chaos founders make is that once they know something will work, they may become less interested in it. For them, exploration is the fun part. Once the mystery feels solved, they lose motivation. The error that both types make is to under-value the opposite trait. We tend to prioritize our own spike. **The scaling PMF phase** This is about doubling down on what works, including things like building up big sales organizations, or scaling globally. The high conscientiousness founder doesn’t need much help here. If a high chaos solo founder reaches this stage, their paths to scaling include: 1. Delegate. Add a very competent exec with a strong DNA match to them and the org. 2. Change. Hire a bunch of exec coaches, get a bunch of CEO mentors to try and absorb conscientiousness via advice and osmosis. 3. Step down. Though when a founder hires a CEO to replace them it often feels like they’re giving up. It’s perhaps better to stay within the business and add people around them, so that the business doesn’t lose the founder DNA. 4. Do nothing. And probably stagnate. High chaos founders who haven’t mitigated their weakness can reach PMF. But they’re unlikely to successfully scale that PMF. This is the first phase where a lack of conscientiousness is critical. **The global platform phase** Once you’re a giant platform, you need to go a-viking into new markets. This requires a new injection of chaos. The high conscientiousness founder will need to find a way to inject fresh energy into the company, to prevent stagnation. The high chaos founder will have only made it to the global platform phase if they’ve already patched their conscientiousness gap. One error that high conscientiousness founders (or hired CEOs) make in this stage is that they no longer value chaos, because it’s been such a long period where conscientiousness has been the most important thing.  **The implications** It’s important to be fully aware of: a) your type (high chaos or high conscientiousness) b) your phase c) unique aspects of the market you’re in and d) the mitigation strategy you’re using for your current phase and next phase. To get a sense of your traits you can inventory the portfolio of your prior projects like an investor might. What have you historically done? How much effort did you put into each? What results did you get from each ($, status, user love, retention, engagement, etc)? The high ROI ones are the market telling you where your strengths matter most and your weaknesses matter least. The main challenges are the phase transitions.  The main advice is to surround yourself with your opposite type. You’ll categorically undervalue the opposite trait. Don’t force yourself to get a cofounder, but do be aware of your gap and surround yourself with some people who excel at the opposite end of the spectrum. This gives you a) osmosis and b) the option for cofounders and c) the option for execs later.  Your weakness *will* bottleneck your strength. The breadth of a high chaos type will be bottlenecked by conscientiousness once the aperture starts narrowing. The depth of a high conscientiousness type will be bottlenecked by a lack of exploration (chaos) to find the global max or a local max. High chaos founders can still do high conscientiousness activities, and vice versa. Think of it as which tasks are energy efficient and which are energy inefficient, not which tasks are possible. It can still be worth it to do energy inefficient activities when you’re aware of the inefficiency and you still expect the payoff is worth it.  Both traits are spikes worth doubling down on, too. You want to get your bottleneck/weakness trait to “just enough”, and your spike/strength trait to “max”. Your bottleneck will determine your floor and your strength will determine your ceiling. Don’t contort yourself, just find the easiest ways to reduce your bottleneck. Consider intentionally surrounding yourself with exceptional people on the opposite end of the spectrum.  --- Who are the high chaos types (founders, investors, otherwise) that have very successfully mitigated their weakness? And vice versa. We’re interested in suggestions: [DM](https://x.com/chrisbarber) or [email](mailto:[email protected]) Chris.