the beginnings of piertree

A finance-focused, creative holding company - a recap of the first 22 months, from a personal perspective:

June 5th, 2022

In this episode I share my journey of starting a financial advising business, Piertree Planning, which later evolved into AllStreet Wealth. I talk about:

  • Door-to-door sales
  • The idea & the plan
  • Saving money & quitting my job
  • Failing licensing exams
  • Doing DoorDash
  • Having my car stolen
  • Having no money
  • The value of Twitter DMs
  • The world of freelancing


breaking down the businesses:

July 27, 2022

As of recording, I have 3 businesses and 2 are currently making money:

Piertree is the holding company

AllStreet Wealth is a financial planning and investment management firm

Converting Attention is a modern (financial) design studio

Creatorbread is a blog and newsletter that focuses on making money & business more approachable for self-employed creatives - so freelancers, YouTubers, creators, artists, anyone that’s out there making things and living without a 9-5

While it sounds like a lot, things are starting to compound.

In the first year of business, I made $2,000 total ($6,114 from freelance work, $4,219 business losses)

But now, I’ve already made $31,000 in my second year (from July of last year to July of this year)

So technically from year one to year two, I 15x’d my income.

While that obviously isn’t sustainable, I’m on pace to make $50,000 next year if everything stays the same and nothing big breaks through.

It could be more than that, but I’m working really hard to make sure that it’s not less.


the story of allstreet:

September 20, 2022

As of recording, it’s officially been 365 days since I made the decision to bring on a partner into the business.

Since then, we’ve gone from a little over $3,000 in monthly revenue to hitting $15,000 last month.

But first, if you’re new here, here’s a little bit of context on my story:

In June 2020, I quit my 9-5 job and started a financial planning firm called Piertree Planning.

The goal was to work with my generation.

After a few months, I had some clients but was barely covering business expenses.

So I was doing DoorDash to pay my personal bills and eventually came across personal finance freelance writing as an opportunity.

Almost immediately, I fell in love with it.

So in Spring of 2021 - about 8 months after starting the business - my idea was to grow as a freelancer, shut down Piertree Planning as an RIA, and just offer financial education content, maybe some courses for freelancers and self-employed people, and completely change career paths.

But a different opportunity came up about 2 weeks after I had those thoughts.

One of my financial advisor friends, Justin Castelli, reached out and asked if I would be interested in hiring someone or bringing on a partner to the business as the advisor he had working for him, Thomas Kopelman, was growing too quick for his firm.

We agreed, I drove to Indianapolis to meet, thought about the new firm, and prepped everything to launch ASAP.
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Financial planning & investment advisory services are provided by AllStreet Wealth. The firm is a registered investment adviser with the state of Missouri and Indiana, and may only transact business with residents of those states, or residents of other states where otherwise legally permitted subject to exemption or exclusion from registration requirements. Registration with the United States Securities and Exchange Commission or any state securities authority does not imply a certain level of skill or training.
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