Founder log · 6-min read

I spent $4,500 on professional photographer headshots over 4 years. Then I tried an iPhone app on a Tuesday.

By HiForrest · Published June 5, 2026

A solo founder's honest math on personal-brand photography. Hint: the photographer was almost never the bottleneck.

Between 2022 and 2026 I paid five different photographers for headshots. I added it up the other night: $4,500, including studio rentals, retouching, and one absurd $200 dry-cleaning bill for a navy blazer I ruined trying to look interesting.

I have used exactly three of those photos online.

What I was actually paying for

In retrospect, almost none of what I was paying for was the photo itself. The photographer takes the photo. The version of you in the photo is decided weeks before the shoot, when you're picking the outfit and the framing in your head. The photographer is the last 10% of the work and 100% of the cost.

The photographer takes the photo. The version of you in the photo is decided weeks before the shoot, when you're picking the outfit and the framing in your head.

The other thing I was paying for was iteration cost. Each shoot took half a day. I'd get back 60 raw images, pick 4, and discover months later that the lighting was wrong for the new brand color, or I'd cut my hair, or the season changed. Re-shoot. Re-iterate. Re-pay.

Same person. Four prompts. One selfie. ArcFace likeness 0.913 — measured, published, reproducible.

What broke the loop

A friend who runs an agency texted me one Tuesday: "have you tried HeadshotMax? Took a selfie at lunch, four styles in a minute, kept three." She sent the result. It was her — same face, same hairline, same the-eyes-she-actually-has — in a Formal Corporate look that would have cost her $700 at the studio she usually uses.

I downloaded the app. Took a selfie at my desk. Paid the $2.99 to see the preview. Got Tech Founder, LinkedIn Friendly, Executive Boardroom, and Editorial B&W back in under a minute. Two of the four were better than my last paid shoot. I upgraded to the $35 pack, got 50 images at 1024×1024, used the credit back so the effective spend was $32.

The math

That's a 99.3% reduction in cost ($4,500 → $32) and roughly a 200× reduction in time (half a day → 4 minutes). The relevant comparison isn't quality-against-quality — the studio photo still wins on absolute image quality. The relevant comparison is whether the difference in quality is worth the $32-vs-$4,500 spread and the half-day-vs-four-minute spread.

For everything below "this is the headshot on the back of my book," it isn't. For the back of the book, hire the photographer.

Pay $2.99 — see your preview

Credit applied to any upgrade. No free-tier tease, no watermark.

What changed about the work, not just the photo

This is the part that surprised me. When the iteration cost of a headshot dropped to near-zero, my willingness to experiment with how I present myself online went way up. I tried a Formal Corporate for the consulting page, a Tech Founder for the startup page, an Editorial B&W for the speaking bio. I A/B-tested which one converted better on the email signature.

That experimentation was simply not on the table when each iteration cost $400 and a Saturday.

What I'd tell a younger founder

If you're a solo operator and you're about to spend $400 on a single set of headshots: don't. Spend $2.99 first. See the preview. If it doesn't look like you, you've lost the price of a coffee. If it does, upgrade to the $35 pack and you have 50 images across 4 looks. If you decide later that you really do want the studio polish, you've still saved about $360, you've already locked in three usable looks, and you'll show up to the studio with a much clearer sense of what you actually want.

I'm not anti-photographer. I'm anti-spending-half-a-day-and-$400 to find out the lighting was off.