profile

Let's Build with Shegun Otulana

The Tuesday Roundup

Published 5 months ago • 1 min read

The classic book on tipping points is Malcolm Gladwell’s The Tipping Point. Read it to grasp what a tipping point actually is, and be inspired by the stories of small actions leading to great outcomes in business and life.


Reaching your tipping point requires a commitment to doing the same small things over and over, getting better each time. It means letting go of the idea that all of your work will be exciting all of the time. This article by John Cutler is a reminder that the “boring bits” are what lay the foundation for success.

It is easy for a team to quit after a couple tries and get overwhelmed with a new, shiny project. Many teams treat the meta-work as something you do on top of the "real" work. There's no time. But if you keep at it -- take the leap of faith, and carve out the time and energy -- there's a good chance your team will benefit.


Experimentation in the product and customer acquisition is how you iterate toward your tipping point. Your experiments should teach you what works and what doesn’t so you can keep optimizing. In order to learn from them, your experiments have to be well-designed. This guide will help you set up experiments that produce clear learnings.

The single worst thing you can do that will waste your company’s time and money is to start working on the experiment without a clear, measurable goal, and underlying hypothesis. Goals like wanting to increase the number of sales or conversions are common, but it’s not enough to build up an experimentation engine that increases your long-term conversion rates.


You may have to experiment and iterate for a while before you reach success, but you have to stay in the game long enough to reach your tipping point. It’s unlikely that you’ll discover a single silver bullet that leads to instant success. David Cummings has a great reflection on how to stick it out, including some practical tips to make it work.

Startups are incredibly hard and figuring out how to survive so that you can be at the right place at the right time makes all the difference.

Let's Build with Shegun Otulana

Helping you bootstrap to a billion.

Read more from Let's Build with Shegun Otulana

Clarity Needed​ Recently, I was having a conversation with a leader of a company in my portfolio. It's a small team doing well in its early days but navigating some inflection points. We were discussing a key team member. She appreciated that he did good work on individual tasks, but she was concerned about some critical decisions he was making and the ideas he was putting forth. His ideas didn't align with her business direction and vision. The team member seemed very excited and couldn't...

8 days ago • 1 min read

The Tuesday Roundup​ Today I’m sharing more resources to help you make great decisions. Andy Grove, as I mentioned in the newsletter, is a great resource for leadership and decision making. Read his classic book on business leadership, High Output Management for insights on decision making, innovation, and business execution.​ It can be difficult to know how to put yourself in the “knowing what I now know” mindset. This article from HBR explains different ways to get yourself out of a biased...

17 days ago • 1 min read

Knowing What I Know Now: Making Great Decisions​ One of my favorite entrepreneurship stories is about Andy Grove and Gordon Moore, the founders of Intel, during a difficult phase of the company's business. Intel had found significant success in the memory chip space. It was a growing market, responsible for most of Intel's profits. However, stiff competition from Japan, among other factors, was beginning to affect profitability. It was getting commoditized. Andy and Gordon were torn. Memory...

22 days ago • 2 min read
Share this post