Post-Acquisition Lessons on Time & Energy Management: What I'd Do Differently as a Repeat Founder

I’m a tech entrepreneur that has been building startups for the last 11 years.

My last startup, ListenLoop was acquired in 2019. Then I spent three years at the parent company, a fast-growing B2B startup on a path to its IPO. A few months ago, I got the itch to start another venture–this time in web3.

To turbocharge my crypto-pilling experience, I joined the Consensys Mesh: Tachyon accelerator for web3 startups. I’m now in the second week of the program, and Tachyon mentors often ask, “how’s it going?” I strive to give authentic responses, and I recently said,

“Honestly, it's exhausting. Mostly in a good way but exhausting nonetheless. I forgot how much energy it takes to go from 0 to 1.”

As a sucker for time travel stories (Time Cop, Terminator, Interstellar), I've often fantasized about coaching my younger self to be better.

This post explores what advice I'd give myself when I was launching my last startup.

My hope is that you benefit from my reflections and that this post counsels my future self, too. Should Future Me stray, may this post bring him back to center.

What is 0 ➡ 1?

According to Peter Thiel, there are two types of innovation. If you take something that exists and improve upon it you go from 1 to N. But creating something new means going from 0 to 1.

I think of those moments as shaping clay. You mold it and mold it until you have something beautiful.

Clay is given shape by pressing a vision into its malleable form.  Like clay, startups must be given shape and direction for them to become valuable.

But many times, we start in a direction and find that there's no product-market fit. Or perhaps the product is not solving a big enough problem. So you grab the clay, mash it into a ball, and try again.

Shape. Mash. Shape. Mash. Shape… it's an exhausting process. If you’re not familiar with the amount of time and effort required, you might quit each time you restart because trashing earlier work is draining.

But with enough energy–directed at learning more about users and their problems–you can eventually shape the clay into something valuable.

Therefore, the key insight is to conserve energy and then focus it on the actions that best accomplish your goals.

How can I have forgotten such an obvious lesson?

I blame a romanticized memory of running my last startup.  I easily remember the good moments and have to dig for the bad memories. But they're there.

Thanks to recency bias, the strongest memories of my last startup were in 2018, when we were growing profitably, which led to our acquisition in Jan. 2019.  It's harder to remember the earliest phases, when we started in 2013.

While I recall the big pivots (e.g., moving from feedback collection to advertising tech), it's hard to recall the feelings of uncertainty, exhaustion, and frustration.

I'm reconnecting with those earlier feelings as I work on my next startup. The most powerful feeling that I'm rediscovering is excitement.

I find myself waking up at 3 A.M. most nights with my mind racing, thinking of all the things I want to accomplish next. I try to resume sleep. But if I fail after 30 minutes, I get up and start executing. While that sounds like I'm leveraging my excitement, I know it's not sustainable.

Here's my game plan to survive the 0 ➡ 1 phase.

A Better Plan for Time & Energy Management

First, I regularly define my “Big Rock,” which is Tachyon-speak for a week-long OKR. Stemming from that weekly objective, I brainstorm all of the things I could do that week to accomplish the task.

Then I rate each task using a RICE framework to determine which activities will be most far reaching and impactful given the least amount of effort multiplied by the probability of accomplishing said impact.

(Here’s the source Google Sheet if you want to riff on this for yourself.)

Then I determine how much bandwidth I want to allocate on those tasks. Without a time constraint, it’s tempting to say, "let's do it all." Constraints breed creativity.

For example, I budgeted 70% of my time against my Week 2 Big Rock. That translated to 28 hours per week, or 5.6 hrs per day, focused on my objective. Knowing that there are limited few hours to accomplish the goal forced me to think and focus my energy.

Next, I time myself while performing tasks. This is the best way to keep myself on track. I use Toggl.com because it's free, simple, and unobtrusive. My timer safeguards me from web3 rabbit holes.

Before using a timer, an hour could pass by consuming the latest crypto news, Discord channels, and Telegram groups without accomplishing the task at hand. (Plus, keeping time is a throwback to my law firm days when I tracked work in 6-minute increments.  I never minded it much, and I enjoy reviewing the week’s efforts to find opportunities for optimization.)

At the end of each week, I perform a retrospective against my objective. Was I able to accomplish the goal? If not, why? Did I budget enough time to accomplish the objective? Did I underestimate the impact of the chosen activities? This exercise helps me quickly change directions as I plan next week's goal.

The 0 ➡ 1 phase requires unbounded energy. But small bursts of focused energy are better than long periods of distracted effort. Again, the timer helps here. So does drinking plenty of water. I average 8 oz per hour, which is great for hydration but also enforces bio-breaks every ~60 minutes 😅

Aside from better time and energy management, I seek to meditate more.  Truthfully, I used to think meditation was a waste of productive time.

You want me to slow down for 15-minutes? No way.

I was wrong. After completing “21 Days of Calm,” I learned that meditation leads to mindfulness. Ten years ago, I would have grumbled, “WTH does that mean?” Stated simply, meditation improves my ability to enjoy food, friendships, and other life pleasures.

Here's the insight I didn't understand before: focused, mindful enjoyment of life's little moments means that you burnout less when you're struggling to push big rocks up the mountain.

Endure as Long as You Can

As Alex Michelsen (Hedgey Finance) aptly reminded me earlier this week: repeat founders love the 0 ➡ 1 phase – even when they're getting punched in the face by customers, or the lack thereof. It’s true, I do.

It's certainly hard – not to mention demoralizing – when people don't want what you're building. But with enough energy, endurance, and insights, you can eventually find product-market fit.

The important thing is not to burnout in the process. And while molding the clay is rewarding in itself, it pales in comparison to the joy of others marveling at a great product you put in market.

I wish I could have given myself this advice ten years ago. May you find it useful on your journey now...