The Delegation Flywheel

Hey y’all — last call to join myself and beehiiv’s Tyler Denk in Costa Rica for our founder mastermind.

We’ll be working, vibing, and going deep together with structured mastermind sessions. Other details:

• Everyone will have their own private room and bathroom

• Private chef and food are all included

• All activities are optional but included (surfing, yoga, private boat, in-house massages, etc).

• Dates: Wednesday February 25th to Sunday March 1st

• Cost: $10,000 (business write-off eligible).

Expect killer founders, mindset-shifting conversations, and good times.

Anyway, here’s today at a glance:

🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

• Nikita Blanc on how he earned with 0 warm intros (Link)

• Toby Egbuna on how to get your first 20 investor meetings (Link)

• Sunny Dhillon shares his pitch pet peeves that founders should never do (Link)

• Illai Gescheit shares points that will help when an investor is ghosting (Link)

• Sandry Kory shares his thoughts on investor scrutiny of Seed pitch decks (Link)

Growth

• Lotanna Ezeike shares a simple app growth loop (Link)

ICYMI

• Dmitry Shapiro on monetizing AI image and video generation, live (Link)

• Aman Goel shares how startups get acquired for millions (Link)

• Peter Yang shares 25 things he believes in to build great products (Link)

• Aditya shares The Startup Graveyard (Link)

💡 Opportunity: Elder Care App For Managing Aging Parents

With birth rates continuing to fall, we’re going to see more capital be allocated towards ideas that help seniors.

This makes sense — younger generations are busier than ever, more likely to live further away than in the past, and there are simply fewer of them but seniors will still need support managing parts of their health and lives.

The last thing they or their kids want is for them to have to manage a bunch of devices and notifications on their own.

An app that acts as an aggregator, that alerts and summarizes health trends for trusted members of their family, would be genuinely useful. It could also provide a more streamlined way of managing their own health, with all of their considerations in one place.

🧠 Framework: The Delegation Flywheel

I know a bunch of founders who’ve hired assistants in the last year or two for the first time.

Only some of them actually made it work for them on an ongoing basis. It’s not that the others were lazy, they just never set up the right system.

They’d delegate some tasks, their assistant would make mistakes, and the founder would think it’s faster to just do themselves instead.

But delegation doesn’t exist in a vacuum. It has compounding returns, when done right, and gets better every time you use it.

Here’s a simple framework from Aaron Hayslip:

1. Create a doc outlining the steps of a task or process you want your assistant to own

2. They execute it

3. You review the outcome and give feedback

4. The assistant updates the doc based on your feedback relative to their initial understanding

Most things you actually want to delegate to an EA are time-sucking, recurring tasks in the first place. One-offs exist, sure, but the highest leverage things an EA can do are the ones that free your time up in a meaningful, indefinite way.

📈 Trend: AI as a Healthcare Ally

Which of these stats from OpenAI’s internal research surprises you the most:

• Over 5% of all messages sent to ChatGPT are about healthcare

• 1 in 4 active users of ChatGPT ask it healthcare questions every week

• Over 40 million people ask ChatGPT about healthcare every day

Regardless of which you picked, it was shocking to me at first that healthcare makes up that big of a chunk — but it makes sense when you think about it.

Healthcare is super complex, high stakes, and interacting with just about anything in the industry is a terrible experience.

Obviously, healthcare is a highly regulated industry and so breaking into it with new products has unique challenges, but it’s clear the opportunity is here — just like with anything else, asking ChatGPT is good but interacting with an LLM-based product specifically engineered for the industry / problem is better.

💬 Quote: Risk Is Opportunity

The best things in my life have always come from the times when I’ve taken the most risk.

• Moving to a new city without knowing anyone and meeting incredible, lifelong friends.

• Putting $25k on my credit card to rent an Airbnb for a month, without a job at the time, that ended up turning into a company we raised $23M total for.

You get the idea.

Real opportunities close fast (especially in startups, where billions of dollars in VC capital is actively looking to jump on them), so you have to be willing to take risk in order to achieve great things.

You won’t always be right, and failure hurts, but if you take the time to understand why you failed it will do more to help you (by training your risk assessment skills) than hurt you in the long run.

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