Take money when offered
And learn to say no when it is not
I have a money problem.
I avoid making money even when it is there for the taking.
As someone who has an MBA from Stanford, worked in investment banking and restructuring, and operated a search fund, you might think that my money problem is that I am too eager to make lots of money. But my money problem is kind of the opposite. While I would like to make a lot of money, I hate the type of work that pays a lot of money. So I don’t.
The last time I received a regular paycheck was in the fall of 2010 when I shut down my search fund (where investors financially support an entrepreneur's efforts to locate, acquire, manage, and grow a privately held company) because I felt called to help millions of young people escape conventional schooling environments. I’ll spare you the details, but it was the beginning of an all in, very values driven, idealistic type of lifestyle where I was convinced that I needed to sacrifice pay to ensure the future of the projects I was working on, or to ensure that the projects were financially accessible to others. It would not be entirely inaccurate to say that I had a martyr complex.
To bridge some of the gap between not making money working on the projects I really cared about and surviving, I began to charge money for the college and MBA admissions consulting I had already been doling out for free to friends and family. But because I have a money problem, I gave steep discounts or free consulting to friends of friends and anyone who said they could not afford my consulting fees. I left a lot of money on the table.
Beginning in 2016, when I opened my alternative school, I told everyone who came to me for admission support that I was no longer consulting due to conflicts of interest.
But after I shut down the school this past summer, a fellow alternative school leader reached out for advice on getting their unschooled child into a highly selective college overseas. We set up a call where I told them why the plan they envisioned would not work, and I walked them through the steps needed to properly position their child for acceptance. Our call ended with a request to pay me. And I refused.
Them: How much can I pay you for your time?
Me: Don’t worry about it. I’m happy to help.
Them: But this has been so helpful, I feel I should pay you.
Me: No, really, I don’t want you to pay me. Just pay it forward.
I have a money problem.
And I kicked myself for not taking money that someone wanted to pay me. Particularly given my financial situation. I had chosen to go unpaid the first five and a half years running my school, and then paid myself only $1,000 a month for 6 months, and then $3,000 a month for the last year my school was open. Choices that I would never recommend to anyone else. And now I am an unpaid stay-at-home dad. If not for myself, I have a duty to my child to accept payment for my time and services. I sat with that for a long time.
I decided that I needed to establish some guardrails to prevent me from unpaid or underpaid work that would take me away from time with my family or other projects that I want to work on. I set a minimum rate of $500 per hour for a one time engagement, and a minimum rate of $350 per hour for an extended project, inclusive of the time I spend reviewing or editing applications. While such a rate may seem high for some folks, the point is that I need to value my time, and that means being okay with some people choosing to look for cheaper alternatives elsewhere.
About a month later, one week before the early decision deadline for most colleges, an alternative school student I had interacted with in the past reached out to me asking for help.
In the past I would have said yes because I knew the person, and I like to help people, especially people I’ve interacted with in the past. But this time I said, “If your folks were willing to pay for some last minute admissions consulting I'd be more than happy to help out.” I still gave them a considerable discount, breaking the guardrails I had set because I have money problems. I offered a review of their essays and application for $1,000, or a week-long sprint to help them repackage the application for $5,000. The family quickly accepted and paid the $5,000 fee. They could have afforded full price, and I should have asked for it.
I have since established firm prices for the various admissions consulting services I will provide. By referring to the prices I will avoid undervaluing my time in the moment. I have also imposed a zero discount policy that will prevent me from shaving the price upon request or for people I know. It seems the best way to deal with my money problem is to stop being complicit in it.
Recent blog post:
In addition to this substack I plan to write elsewhere. Maybe multiple elsewheres. I don’t know what will stick, and everything will shake out in the end. Here I share an excerpt from my very first blog post on my unfinished saddadical website.
I began to think deeply about how I could continue to work an all-consuming job while raising a child. How could I make myself available for them during the day if I was running the school? Was I willing to put them in child care so that I could continue to work? Could I fully support my child while taking care of other people’s children during the day? Did I even have the energy to support my child while supporting other people’s children, after years of doing so? Or should I get a remote job that would allow me to be more available to them? Would any remote job allow me to have enough time to feel like I was doing enough for my baby?
I decided that the ideal use of my time at this moment in life was to support my newborn baby (and my spouse) by shutting down the school and becoming a stay-at-home dad.
I launched this newsletter with encouragement from the Small Bets community. Thank you to
and for providing wonderful feedback on this essay.