My 1H report card (and yours?)

If you've been following me for a while, you know I like rigor and planning. And guess what? It's that time of year.

Bill Belichick and the New England Patriots (who I hate, btw) are the best NFL dynasty of all time. And, if you ask around why, there's a very simple answer:

So, think of this period as your "halftime:” Step back, look at the first half and then make some critical adjustments.

When we did this at Gateway X, we ran a very simple planning session.

Here was the agenda:

For reflection, use these four simple questions, which I borrowed from Mike Salguero (who bootstrapped ButcherBox to $500M+):

In less than 1 hour, your whole team can feel heard, and you can understand how people assess what’s happened.

Lowlights:

• The market is getting MUCH more crowded and competitive (every Tom, Dick and Harry is doing global talent)

• We still struggle with leadership hires (finding the right person, making sure they’re productive)

• Social content is still our main channel and is less effective than it was

Highlights:

• Our top client accounts are growing (the big are getting bigger)

• The leadership team is working well together to resolve some kinks

• The business is growing steadily with some clear motions (great talent being the first one)

Halftime adjustments:

• We are betting big on marketing and solutions. Our way to win in a competitive market is to go deeper into our area of expertise to create defensibility

• We are betting big on AI (more to come on this), both as part of our offering and to streamline operations

• We are up-leveling talent to accomplish the above. We have a few folks involved now who I'm VERY excited about

Lowlights:

• Our pipeline and business had a "negative" pendulum swing after a few strong Q1s. With huge, chunky deals, it can feel like feast or famine for this young business

• The team has grown quickly, and finance, operations and other "non-delivery" areas are still maturing

• The tariff noise really slowed down PE deal activity

Highlights:

• The team is the absolute best I've ever worked with in terms of smarts, strategy and bias toward action

• The offering continues to resonate strongly in the market

• For all projects, we hit our goal of the 3 Rs (each project either renewed, referred us to someone or agreed to be a reference!)

Halftime adjustments:

• We are slowing down hiring and really trying to stabilize our pipeline to deliver consistent revenue and profits

• We are doubling down on our analytics infrastructure to track critical metrics like BD activity, pipeline, utilization and other areas of the business

• We are experimenting with different offerings in the market to see what sticks

Lowlights:

• The new Accelerator took a bit longer than we hoped to launch, which hit cash flow

• We are still figuring out our 833 offering (our Mastermind) to make it a super compelling and scalable offer

• We didn't love spamming our email list for the Accelerator

Highlights:

• We launched the new Infinity Accelerator with great success — 30+ new students, and it’s off to a great start. It feels like a much more sustainable, long-term idea

• Two full-timers joined and are doing AMAZING. Both complement Andrew and me in great ways

• We had our first conversation about taking an equity stake in a BG company. This is part of our goal of being the YC for bootstrappers

Halftime adjustments:

• We are building the muscle to drive people to the workshop from multiple channels (organic social, paid social, email)

• We are reworking the 833 offering and will relaunch it

• We are planning to hire some new folks to give the current team leverage

Lowlights:

• Revenue is flat to declining

• The debt is high, and the cash flow is tight

Highlights:

• Caith, our new GM, is awesome

• It's profitable, making $25K a month in EBITDA

Halftime adjustments:

• For now, we are still waiting and seeing, but we will either look to sell it, run it down or, if Caith is excited enough, invest a bit more into it to cross this chasm

I won't do the full rundown on Gateway X but, from previous emails, I will tell you, it feels like we are transitioning from being a studio (launching new ideas) to a HoldCo.

I will save a “journal in public” for a future email, but there's a shift happening that I'm still trying to understand!!

jesse