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We advise and invest in sustainable, high-growth startups that do not need VC funding, attract early acquisition offers, and enable fulfilling and free personal lives for the entire team.

We do not advise founders to provide ridiculously high revenue forecasts. We do not push the CEO to work 60+ hour weeks. We do not expect you to “disrupt the world”. We will not demand a 10%+ stake.

This is startup investment and mentorship for the reasonable founder.


About Wandering Entrepreneur

The most productive days of your life can also be your most fun.

Hi, my name is Ian, and I am a Wandering Entrepreneur

In early 2020, I quit my job to start a tech-enabled services and software business with my co-founder, Rob.

Over two years, we bootstrapped the company to 25 remote employees, built out our software product, and traveled relentlessly. I closed my first major partnership from a hammock on a Barbados beach. I hired our first contractor moments after finishing a spike ball match in Palm Springs. I received our first M&A offer while sipping wine on a cobblestone street in Porto.

I negotiated M&A terms while overlooking a pool in Maui, and in late April of 2022, we were acquired with attractive terms at the height of the market. Two years of traveling and hard work, and we ended with an outcome that was beyond favorable for a couple of twenty-somethings.

In the months following the acquisition, I frequently reflected on the notable lack of mentors and investors we encountered that wanted to help us. Many investors we spoke to refused to consider us if we did not aim to raise $1M+ in our seed round. Traditional investors only wanted to talk to founders that said they would be the next billion dollar unicorn, and we would often be stereotyped as “just a lifestyle business”.

We were much more than “just a lifestyle business”. While our startup contributed to a healthy lifestyle for the founders and employees, we also always targeted (and achieved) explosive growth.

I know firsthand there are strategies that enable a balance between healthy growth and healthy lifestyle. I believe startups that achieve this balance are more sustainable and ultimately make better individual investments. Thus, I created Wandering Entrepreneur.

Wandering Entrepreneur targets a different startup archetype:

Are you in the early stages of a new business venture? Perhaps we should chat!

A couple questions:

 Are you building a B2B SaaS or tech-enabled services company?
Are you hoping to primarily bootstrap / avoid institutional investing?
Are you targeting a quick exit (<5 years)?
Are you looking for strategies to balance work and personal life for yourself and your employees?

If yes to all of the above, I’d love to talk shop! I can almost certainly offer some insights from my own experience.

Fill out this quick form and I will reach out if we are a good fit.

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