The Lifestyle-Founder Vibe Shift.
The Lifestyle-Founder Vibe Shift.
Founders today are mixing growth with fun and avoiding the VC grind.
Welcome to The Elevator. I’m David Sherry. I used to run a business, and now I partner with a dozen or so entrepreneurs building businesses from $1-$25M+ in revenue.
This letter shares the opportunities, trends, and products that stand out.
Here’s what I’m seeing…
When I used to meet someone new and they heard I owned a business, the first thing they asked me was always: “How many employees do you have?”
I always found this an interesting metric to judge the business by.
In the old world – people/labor was how you got scale. Today you get it through code and distribution. Shouldn’t it be the opposite? How BIG of a business do you have relative to how few employees? Being a bootstrapped founder, efficiency was of the essence. It was a necessity to work smarter.
Software unlocked scalability with code instead of people.
Niche software (i.e. not globally dominant winner-take-all-software) created the opportunity for small teams to tackle smaller problems in bigger markets with great margins.
Founder + Lifestyle Entrepeneur = Why not both?
So what is this new category?
Are they founders? Lifestyle entrepreneurs? They’re sort of a mix of both. They want to grow but not so fast as to have the wheels fly off. And definitely not in the VC structure of growth at all costs. They raise smaller funding rounds, get creative with debt, and want to have more fun.
What they are realizing is that success to them is not just a financial metric. And success certainly isn’t headcount.
There are other metrics of success to track like…
Wellbeing and Health
Unlocking their own potential
Doing something fun/cool/weird in the market only they can do
Being surrounded by and working with great people
Making a splash in the market with a new product or concept
AND have a $50-$100M exit.
What else are these founders focused on?
How many employees do you have → How do we hire flexibly?
Moving from default full-time to contractors, agencies, specialists, contractors, coaches, and facilitators. Part-time flexible work, fractional CFO’s, channel-specific social agencies.
*I do feel this will create less on-the-job training, and more needs for external and self-directed learning.
Smaller, more creative funding rounds, done upfront.
If companies can hit scale with less employees, they can also do so with less funding. More founder control in funding, more creative funding mechanisms, using debt, raising money from friends and family. Raising capital up front to be less on a continual funding hamster wheel.
Hiring good people. As in kind, not just smart.
Having a higher filter bar for ‘people I like working with’ as a credential. A no A**holes policy because who wants to deal with that regardless of their talents? Hopefully, this includes the entrepreneurs!
Networks and collaborators over competition.
These entrepreneurs are less likely to get caught up thinking about their competition. They see themselves more in a market that is expanding and less zero-sum. They learn from and respect their competitors, even while they seek to differentiate. Competition forces you to explore your own unique identity further and that’s a worthy challenge.
Freedom, Control, and Happiness
If you cringe at this list, consider that there is a younger generation who…might not.
There will always be a cohort of entrepreneurs who choose to aim for total market domination. The Sam Altman’s of the world will seek to make a global impact. I’m happy to see that, but am just last happy to see people who ultimately dont’ want that for themselves put them in a position to have more control, flexibility, and freedom with their businesses.
How do you think about running your business to scale and grow without putting yourself in a position that you want to avoid? What is the balance of your ambitions with your personal and lifestyle desires?
As always, let me know how I can help.
xx David
I’m David Sherry, prev founder of Death to Stock. I partner with founders & entrepreneurs with growing companies. Helping them define their vision and grow personally and professionally to capture their biggest opportunities.