About Deliberate Entrepreneurship

Good things come to those who wait”

Not so in the world of entrepreneurship.

Stop waiting for inspiration to hit. You can vastly increase your chances of finding opportunities by getting out there and looking for them – and there are tried and tested ways of doing so.

Stop trying to figure it out alone. You’re not the first person to face the creative challenge of turning your seed of an idea into a successful business – you can leverage the learnings of those who’ve gone before.

You can decide to become an entrepreneur today.

These articles will show you how.

Deliberate Entrepreneurship:

2 Core Beliefs

Belief 1:

You can deliberately decide to become an entrepreneur today – with or without a business idea

  • Deliberate entrepreneurship means deliberately looking for entrepreneurial opportunities. It is a proactive, systematic approach to finding attractive business opportunities
  • Deliberate entrepreneurs don’t wait patiently for inspiring business ideas, instead they follow a deliberate process to find them. While other entrepreneurs may haphazardly stumble upon a business idea, deliberate entrepreneurs go out and proactively hunt them down
  • Deliberate entrepreneurs can make money from day 1, working and living sustainably as an entrepreneur

Belief 2:

You can influence your chances of finding an attractive business opportunity – and you maximize those chances by first becoming an entrepreneur

  • You can start working as an entrepreneur before you have an idea: you can find other people’s ideas to test and build.
  • Ideas cannot be forced, but you can maximize your chances of noticing an attractive one
  • You are most likely to find opportunities by thinking like an entrepreneur, and the best way to think like an entrepreneur is to become one.

The only idea you need to believe in is the idea that you can (and want to) make it as an entrepreneur.

Note: Leadership Positions at Early Stage Companies

When I refer to “working as an entrepreneur” I limit the definition to include only leadership positions (~CxO roles) at early stage companies.

This includes working on your own company or someone else’s.

This does not include :

  • Working as a VC: these roles entail looking for opportunities, but not testing or building them as an entrepreneur
  • Founder’s Associate / Entrepreneur in Residence roles: there are exceptions, but in general, although these roles can involve hands-on experience testing opportunities (and are a great place to start honing your skills), they do not entail the high stakes, leadership level decision making opportunities required of entrepreneurs

My experience of Deliberate Entrepreneurship

I’ve been a deliberate entrepreneur for the past 6 years, many of my peers are deliberate entrepreneurs, and I’m an Executive Coach to multiple successful deliberate entrepreneurs.

After beginning my career as a strategy consultant at BCG and as a tech M&A advisor, I’ve spent the last 6 years working full-time as a profitable entrepreneur:

  • I’ve tested 20+ businesses, 3 of which generated $1m+ in sales
  • At my last business, Advisable.com, my cofounder and I raised $1m VC funding, grew 20% MoM for 2 years to $200k monthly bookings, then raised $3m in the middle of the pandemic
  • I’ve spent 2021 training and working as an Executive Coach for entrepreneurs, coaching & mentoring 100s of entrepreneurs at leading accelerator programs (Techstars, Entrepreneur First) and in my private coaching practice

For context, I spent only ~6 months of those 6 years working in leadership roles at other people’s startups. The rest was spent as co-founder/founder of my own businesses.

What experience do you need to become a deliberate entrepreneur?

This is written for any smart, ambitious person who believes they can make it as an entrepreneur. The same approach applies whether you’re looking for your first or your twenty-first opportunity.

That said, there are certain things that can increase your probability of success. Ultimately, this will depend on whether you want to first work on your own ideas or other people’s ideas:

  • Some savings/resources, ability to earn money and sell yourself
  • If you’re looking for opportunities to test other people’s startups in a leadership role, then having a couple years’ work experience and an existing track record of success will help

Here is the experience I had:

  • I left BCG with 2 ideas and 3 months runway – I didn’t find an opportunity
  • I left my next job with no ideas and 3 months runway – I did find an opportunity (and haven’t looked back since)

When I became a deliberate entrepreneur I had:

  • Business experience and a demonstrable track record of high performance / good brand (BCG; M&A)
  • A demonstrated interest in entrepreneurship (I had my own business in Uni) 
  • A basic network to start from (from ~4 years work experience)
  • An entrepreneurial mindset (this was the key difference between my early failure and later success)

I didn’t have:

  • Any direct startup experience: if you’ve already worked in a startup, it will be much easier to open doors (especially if you’ve done a great job there)
  • Any tangible skills (product mgmt; marketing; tech): I could sell my ability to execute, but I didn’t have direct evidence of it. If you have tangible skills that are in demand by startups, then you’ll have a much easier time

As a general rule, the riskier the proposition you are perceived to be, the riskier the pool of opportunities you will have access to. The benefits of this is that there is a lower opportunity cost to pursuing your own ideas!

Who makes a good deliberate entrepreneur

Some characteristics of successful deliberate entrepreneurs include:

  • In tune with intuition: deliberate entrepreneurs are intuitively drawn to entrepreneurship, they have a powerful belief that they will be most fulfilled as entrepreneurs. Even before they have clear ideas, they are drawn towards a sense of opportunity in certain spaces or types of business. It can be difficult to follow these early senses of opportunity (first tastes of uncertainty; path not clear), but it’s far more painful to avoid following them!
  • Driven to explore: following one’s intuition requires learning to explore. This is an important skill that can and must be learned. Early stage entrepreneurship is characterized by a high degree of uncertainty: there are many unknown unknowns. The benefits of desktop research are limited. Talking to existing founders in an area will unlock perspectives you’d likely never considered. Testing different opportunities is a prerequisite to effective evaluation
  • Committed: deliberate entrepreneurs are explicit about their various levels of commitment. How committed are they to the process of finding an idea? Some are so committed that alternative routes simply don’t exist in their mind; for others it’s a more tentative commitment. How committed are they to testing a particular idea? What does this commitment look like (time, money, milestones etc.)? 

The goal of this series of articles is to enable you to become a better deliberate entrepreneur. I explore the best practices of the most successful deliberate entrepreneurs, based on my own experience, the experience of my peers and the experience of my clients.

Q: In what ways are you drawn toward deliberate entrepreneurship?


Sidebar: Working with a Coach

As you embark on this process of deliberate entrepreneurship, I believe that a good coach is 100% worth the investment: you will make progress a lot faster, find better opportunities, execute at a higher level – and experience a lot less pain

  • A good coach can increase your performance and likelihood of success in any difficult endeavour
  • Deliberate entrepreneurship is one such endeavour: the level of uncertainty is high, there are many ups and downs and it’s hard to maintain perspective

Whether or not you decide to work with a professional coach, it is vital you identify and build a support group of peers and/or mentors

Leave a comment

Your email address will not be published.