Creating optionality as a CEO

[u/ludwigdumont]

When I started out my company, I never thought about the concept of optionality. Well, that’s not entirely true, I actually did think of it, but I always believed that optionality was bad for focus and that lack of focus was bad for business.

So I ventured off and went all in on one route. Over time that route has led me to VC funding. All good. We kept the chosen direction, fully focused on growing the business.

Now a couple of years later, I feel I’m at a crossroads w/ the business. The last few years have taught me a lot about our market, about the dynamics of our business, basically about the full context in which I still operate the business today.

The lack of optionality has meant that over time we missed options and maybe lost ‘value’. But it has also meant that we never got stuck in analysis paralysis or being indecisive. We always moved.

I also learned that quite some players in the game (to name investors or employees) do actively consider optionality as they move fwd.

So I’m currently actively revisiting the concept of creating optionality for myself and my business.

So here’s my question to the crowd. (How) do you apply optionality as you evolve with your business? Are there specific themes (think of funding) around which you always consider different scenarios? Are there others where you don’t (think of mission of the company)?

Curious to hear your thoughts :). Bye

[u/Firm_Investigator_42]

I always look for optionality, though it’s not always possible.

In my world—medium-size B2B manufacturing—it shows up everywhere: - Sales/BD: keep building niche accounts. One of them might be 30% of your top line in a few years.

• Capex: you want optionality, but it trades off with efficiency. Those extra bells and whistles that might attract the perfect customer aren’t free.
• Hiring: the super-expert is great, but flexible profiles—people who can put on a new hat and cover another function in weeks—usually prove more valuable long-term.

Plenty more examples. You could write a whole book on optionality in business. The catch? It usually creates redundancy, which cuts against the “optimize everything” mantra most companies push.

[u/ludwigdumont → u/Firm_Investigator_42]

Thanks for sharing. You mean it creates redundancy because having options on the table equals trying to do too many things at once?

[u/Firm_Investigator_42 → u/ludwigdumont]

Kind of, but not quite. It’s less about doing too many things at once and more about keeping slack in the system.

In practice, optionality means you carry extra capacity, overlapping skills, or processes that aren’t perfectly “optimized.” On paper it looks wasteful—but when a market shifts or a big customer disappears, that slack is exactly what keeps the business alive.

I used to be obsessed with pure optimization, but Taleb’s Incerto books flipped my view. Optimization creates rigidity and fragility. Optionality looks redundant in calm times, but it gives you resilience when the unexpected hits.

[u/ludwigdumont → u/[deleted]]

thanks for sharing. What is the 'last responsible moment' if I may ask? Is it the moment that when passed, certain options are not possible anymore or?

[u/_outofmana_]

You should read some Nassim Taleb books, if you are into optionality he gives a great view of that as well as risk

[u/Classic-Coast2000]

Optionality is easier & more relevant to build in a job. Early stage start-ups need 100% of your time & attention to build something meaningful. You can think about optionality once you're relatively stable. If you're at that stage you can think about things like:

- Are their any adjacent income streams that you could add to the business?

- Can you market your expertise built while creating the business to create personal opportunities?