Reading · On Work by Shaina Anderson

👋 Hey, it’s Shaina, and I’m back for another issue of On Work, the weekly letter on independent entrepreneurship, fractional work, portfolio careers, and more.

If you’re new — hi! Welcome. Help me spread the word by sharing with your friends, and please say hello in the comments.

In the first year of Hello Generalist, nearly 100% of my new business came from one habit. Despite not having a single investor, I sent an investor update.

I had friends, former colleagues, and a few mentors who’d said “let me know how I can help,” and the update was how I told them.

Quick primer in case you haven’t seen one. In the startup world, investor updates are what founders send (usually monthly or quarterly) to the people who’ve put money into their company. A few wins, honest metrics, the stuff that’s hard, shout outs and thank yous, and specific asks for intros, hires, feedback, and advice. The goal is to keep backers in the loop and give them an easy on-ramp to help. The best ones read like a letter from a friend who’s building something. The worst ones read like a board deck.

The beautiful reality is that you don’t need to have taken a single check for the format to work. If you’re building a solo business, your friends, clients, mentors, and former colleagues are functionally your investors. They’ve put attention, time, and social capital into you. The update is just how you activate them. How you open your window and say - Hey! I’m still over here! Come see!

Now in my fourth year, it’s still among the highest-ROI things I do. I send one quarterly-ish now (though it was weekly at the start, then monthly). Every single time I hit send, a handful of near-guaranteed referrals land in my inbox within a week.

I’m also on the receiving end of about ten of these a week from HG customers, operators, Manual Override alums, and founder friends. I read every single one. And almost every time, I end up doing something for that person: making an intro, sending a lead, sharing a resource I’d been sitting on. Being in the loop makes helping frictionless.

So here’s today’s case: if you’re running anything solo (coaching, consulting, fractional work, a podcast, a tiny product), even if you have exactly zero investors, you should be writing an investor update. This is the exact format I use.

“Using your network” feels murky and kind of gross because most people do it badly. You only reach out when you need something. You open with the ask. You pitch at people instead of sharing with them.

An investor update is the opposite. You’re not pitching. You’re reporting. You’re treating the people around you like they already care about your work (because they do), and you’re giving them the ingredients to help you without making them do the work of figuring out how.

The trick: because it’s a status update, your asks stop feeling like asks. “Looking for intros to heads of growth at Series A B2B SaaS companies” lands completely differently inside a monthly recap than it does in a cold DM. It’s also the single most forwardable asset you’ll ever make. People pass these along to their own networks with a note like “you should meet this person.” You cannot buy that.

This is the format we give our crew in Manual Override. Every Friday in MO we run Ship It Friday, where the cohort shares progress on their business, no matter how small. We ask them to use investor update principles for their weekly share, and to keep the habit going long after MO is over. It’s one of the drumbeats that holds the program together.

Here’s the format for you to riff on:

Subject: [Your name or business] — [Month] update

Hey friends,

Coming to you with a quick note on what I’ve been building. As a reminder, I’m [what you do] for [who you help] who want [problem you solve].

Asks. Be specific. “Intros to heads of ops at Series A B2B SaaS.” “A referral for a designer who’s great at landing pages.” “Feedback on this new offering I’m testing.” Vague asks die. Specific asks get answered.

Wins. What you launched, landed, or learned. Small wins count. Momentum is magnetic, and wins make people want to refer you.

Challenges. Be real. This is underrated BD. When you say “I’m stuck on X,” three people reply with ideas. People connect to honesty, not polish.

By the numbers. Revenue, clients, pipeline, downloads. Whatever makes sense for your business. Keep it small and honest.

What’s next. One or two things you’re focused on. Helps people know what to cheer for.

Shoutouts. Lead with gratitude. Name the people who made intros, sent referrals, or showed up since your last update. When someone sees their name, they reply, stay connected, and look out for you next time.

[Then, at the end, include pictures, links, screenshots - anything that shows the work, and makes it even more personal.]

Thanks for being on this list. If you want to unsubscribe, just reply and lmk - no hard feelings.

Warmly, kindly, lovingly, yours in building something wonderful, [You]

Specific asks win. “Intros to marketing leads” is okay. “Intros to a head of growth at a 20–50 person B2B SaaS company” is a referral waiting to happen. The more specific, the more people can actually help.

Don’t wait for big news. The updates I love most are the messy ones. The “here’s what broke this month” ones. Polished updates look like pitches. Messy ones look like humans.

Keep it short. 300 to 500 words. Your friends are busy. This isn’t a newsletter.

Start small on the list. 20 to 50 real people who’ve told you they want to help. Friends, former colleagues, clients, mentors, people who’ve cheered you on, and grow the list from there.

Write like you’re texting a smart friend. No buzzwords. No “Q3 learnings.” No hedging. Just what’s going on in Plain English. You might even use a voice to text software to actually capture your own voice.

There’s also a bunch of great lessons from the startup world. If you want to go deep, I love these articles:

The best part of this isn’t the intros or the referrals (though those are real and they add up fast). It’s that it reframes your relationship with business development. Instead of “ask for things,” the practice becomes “stay in touch generously.” You stop hustling your network. You just let them help you.

Write one this week! Send it to the twenty people closest to your business, and, if you’d like, include me. shaina@hellogeneralist.com.

Investor Updates for people without investors

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