What’s up, founders?!

Short and Sweet one today

• SXSW 🤝 

• Make your employees contractors…for their own good?

• Bali Retreat 🌴 

• Startup Idea 💡 

Find me at SXSW!

I’ll be participating in typical Austinite fashion

This means: I’m registered for like 20 events but I’ll probably only attend 1-4 total. The one I’m most excited about is the Startup Olympics because I am a juvenile at heart.

Wanna meet up?

If you’ll be in Austin this weekend / next week, hit me up! Let’s get a Coffee/Lunch/Beer.

Let your “employees” work whenever they want.

Sahil Lavingia is working earnestly to change the way we employ people.

Why? I believe he genuinely cares about people and wants to see them create their own version of work/life balance (AKA: Freedom). If you don’t know Sahil then you’re probably not really into the tech twitter scene. The short version is that he’s a tech influencer, thought leader, and the founder of Gumroad.

His latest project, Flexile is a SaaS product that helps you “employ” people the way he does at Gumroad which he’s written at length about. He literally wrote a book called “The Minimalist Entrepreneur” in which he writes about how to run a tight ship amid the rise of the gig economy and remote work.

No Meetings. No Deadlines. No Full-Time Employees.

This is literally the title of Sahil’s manifesto on what I’m calling “The Gumroad Way”.

Unlike MANY of you who answered my poll last week about team alignment, Sahil doesn’t believe meetings are the way to go.

He wrote in great detail about the way it works in his 2021 blog post and I can’t help but wonder if the model is applicable to more startups. I’ll summarize:

Gumroad operates in a manner akin to working on an open-source project, focusing on digital collaboration tools like GitHub, Notion, and occasionally Slack, to facilitate communication without the need for traditional meetings or standups. The company emphasizes clear and thoughtful communication, as there are no deadlines, opting instead for incremental shipping based on improvements over existing production offerings. New joiners start by picking tasks from the Notion queue, underscoring a self-directed work ethic.

Rather than adhering to quarterly goals or OKRs, Gumroad's guiding principle is to maximize earnings for creators (Their core users), a goal that is both simple and measurable. This approach allows for flexibility in prioritization, enabling team members to work on projects that are enjoyable or intuitively important, while a public roadmap keeps the company accountable to its creators.

Decision-making on projects often balances emotional investment with practicality, not relying heavily on data analysis but on what feels rewarding and beneficial for their community of creators. Communication is streamlined by minimizing digital interruptions, and the work culture celebrates incremental and iterative developments, highlighted by one significant launch annually.

However, Sahil acknowledges limitations in career growth opportunities within the company, maintaining a focus on profitability over rapid expansion. The company briefly considered transitioning to full-time roles to support growth but ultimately retained its existing model, prioritizing freedom, sustainability, and work-life balance over traditional business growth metrics. Gumroad's ethos, as reflected on its homepage, champions creator independence and financial autonomy, positioning itself as a platform by and for creators, embodying a vision for a work culture that values life over traditional employment structures.

Back to Flexile:

I’m enamored with the new tool that will help other entrepreneurs run their companies similar to Gumroad, where each job posting has a fun little calculator that tells you how much you’d earn based on your ideal number of hours per week and weeks per year.

Give them some equity!

How can you be sure that contractors will work as hard on improving your business as a full-time employee would? Give them some equity. Better yet, let them choose how much equity they take with EVERY invoice 🤯 

Gumroad candidates can check a box on their application that allows them to model out what various levels of “Equity swap” might look like. I love this!

Wanna join 24 other founders on an unforgettable Bali retreat?

Myself and 25 of you will head to Bali in June for the first-ever Founders Only Retreat. The best part? It’s a 100% tax-deductible business expense!

Woooooooooooooooo 🎉 I can’t wait to meet you and I’m thrilled we’ll all be helping each other grow as founders.

The application to attend is simple:

Fill this out by March 14th

Unfortunately for this first retreat, we can only take 25 people so please fill out the form now!

When is this?

The first week of June (2024).

Saturday, June 1 - Monday, June 3 (but you’re definitely going to want to stay for at least a week. It’s cheap and awesome)

What are we going to do?

We’ll all stay in Canggu and we’ll organize a Slack workspace to discuss things like lodging together if you like to save money that way. It’s pretty cheap though; You can find amazing places in Canggu for $500 /week.

A team of great people and I are planning 2.5 days of activities including:

• A keynote and fireside chat with a special guest (I don’t know who, but somebody good)

• A small team hackathon (cash prizes 🤑 )

• Daily organized outdoorsy activities (Surf lessons, beach yoga, cold plunging in nature, etc)

• A day at a beach club

What does the retreat cost?

It’s $500 if you pay your ($200) deposit by end-of-day Monday, April 1. It’s $750 to attend if you miss that early-bird deadline.

YES, it is a tax-deductible business expense.

What is included?

• Breakfast each day

• Lunch 2 days

• Dinner 2 days

• The aforementioned events/experiences.

• Co-working space

• Travel Medical Insurance provided by Insured Nomads

💡 Business Idea of the Week

Pickleball is exploding — It’s the fastest-growing sport in America (3 years in a row)

As far as I can tell, there STILL isn’t a marketplace for LOCAL, IN-PERSON coaching. Sure there are plenty of virtual coaching apps but I want to easily find somebody to meet me at my local court and run me through some drills for an hour.

There’s a multi-niche site called TeachMe.to that is addressing this but with a clunky solution and failure to niche down. Make a handy mobile app and you’re golden.

THE END

Thank you as always for reading this. I don’t have any sponsors, directives, or agenda so you’re always going to get whatever topics inspired me during the week. This one was fun!

I love you all.

Sincerely,

John Hancock

Follow me (or just yell at me) on Twitter