Building companies
Company building
Jake’s firsthand lessons from building companies, developing systems, and working through operating decisions.
23 articles · 19 early essays
Articles
What breaks when a services company grows fast
Fast growth strains delivery oversight, hiring, ownership of functions, finance and cash. What broke as my podcast company grew, and what to set up first.
Essay
How to prepare for business growth
What breaks when a service business grows fast, from delivery and hiring to finance and cash flow: my December 2023 essay on scaling Content Allies.
Essay
How I take new businesses to market
My 2023 routine for a new offer: wait 30 days on an unexpected idea, build a sales deck fast, sell to my network, then go all in on one marketing channel.
Essay
Fountainhead philosophy in business: Roark vs Wynand
My November 2023 essay on Roark and Wynand in The Fountainhead, and the founder's pull between meaningful work and giving the market what it wants.
Essay
My framework for starting a new business
My 2021 checklist for starting a new business: a growing market, the RESCUE test, three sales from my network in about 30 days, then operations.
Essay
Why Entrepreneurs Succeed by Leveling Up as Leaders
My May 2020 essay on moving from doing the work yourself to coaching people to contribute more, with what I said about letting go five years later.
Point of view
Lead Cookie: moving beyond a productized service
Why I was moving Lead Cookie toward hand-qualified outreach in May 2020, the changes it required, and what I said about the business five years later.
Essay
The hard emotional side of entrepreneurship
My April 2020 essay on owner decisions that hurt, like layoffs and pay cuts, and the weekly question and one-week pause I used to stop delaying them.
Essay
The importance of iteration for entrepreneurs
My February 2020 essay on why no business reaches a perfect state, how Lead Cookie's market commoditized, and why I learned to keep iterating.
Essay
The shortcut and shortfall of selling to your peers
My February 2020 essay on selling to peers: why Content Allies' first clients, owners like me, churned, and why I then targeted consultants earning $250k+.
Essay
The evolutions of freedom from your business
My January 2020 essay on the six stages of stepping back from a service business, from doing the work yourself to a company that markets without you.
Essay
Handing off founder-led sales: how I did it at Lead Cookie
My January 2020 account of handing off sales at Lead Cookie: why my first attempt failed, then the playbook, hire and 90-day plan that worked.
Essay
I failed at selling Lead Cookie, here is what I learned
My January 2020 account of trying to sell Lead Cookie in 2019: cleaning up the books, hiring a broker, and an LOI that fell apart in due diligence.
Essay
How We Ran Lead Cookie's 90-Minute Weekly Team Meeting
The 90-minute weekly agenda I ran for Lead Cookie's remote team of about 26 in 2019, built from EOS and Chet Holmes, and what has changed since.
Essay
The art of thinking through your business model
My July 2019 questions for choosing a business model: what you want, ten-year relevance, platform risk, recurring need, agency or product, and the numbers.
Essay
The problem with productized marketing services
Why single-channel marketing services churn by design and work best as a tripwire into an agency: my June 2019 essay, from running Lead Cookie.
Essay
Lessons learned for my second productized service
My May 2019 essay on starting Content Allies after Lead Cookie: reducing platform dependence, hiring before the first sale and growing slowly on purpose.
Essay
What is the "Queen Bee Role" and why does it matter?
My April 2019 essay on the Queen Bee Role from Mike Michalowicz's Clockwork, and how I took admin work off the account strategy role at Lead Cookie.
Essay
The Weekly Metrics Dashboard I Used to Run Lead Cookie
The weekly sheet I ran Lead Cookie on: customers, billed and projected MRR, leads, calls, profit and retention, and what I would add to it today.
Essay
The painful consequences of not focusing
My February 2019 essay on running Lead Cookie, a sales role and consulting at once, what it cost, what focus changed, and how my view shifted by 2020.
Essay
How My Personal Brand Built Lead Cookie’s Revenue
My 2019 account of how my personal brand drove Lead Cookie’s revenue through podcast relationships, and later lessons on who a podcast should serve.
Essay
Sales call script: the seven-stage Lead Cookie framework
The seven-stage sales call script behind my reported 375 calls and 154 closed deals at Lead Cookie, with supporting emails and what has changed.
Practical guide
Productized service lessons: Lead Cookie's first six months
My January 2018 lessons from Lead Cookie's first six months as a productized service, from the first pitch to $33,168 MRR, and my 2019 correction.
Essay
From Jake’s early writing
These essays are kept with their original dates. Explore all early writing.
- Stop overthinking it... take action.
- How Understanding My Unique Ability Changed My Life
- Why decision fatigue is so important for entrepreneurs
- The magic of a money-back guarantee
- The 15-year overnight success behind Lead Cookie
- The Value of Coaching Your Team
- You choose what business you build
- The #1 mistake when starting a productized service
- Lessons from 6 months of advising with Alex McClafferty
- Our weekly company habit that changed everything
- Shutting down my startup: seven lessons from Content Allies
- Before starting a business, ask why you are building it
- Building a business on someone else's platform
- Zero to $60k in 90 days: Launch plan for my new venture
- Stealing business ideas: how I modeled Lead Cookie
- Lessons learned from a year of evolution
- Why creatives should think twice before hiring
- Accepting Failure
- The Courage to Try