Prepared + Lucky: Henry Woodman on Turning Personal Problems into Businesses (and What AI Means for Film & TV)

Guest: Henry Woodman — entrepreneur, producer, author of The Reincarnation of Marie
Show: Interchain.me – Life Tips
Listen to the Podcast

Henry Woodman’s career reads like a field guide to opportunity: coin-op games in laundromats, travel filmmaking, a Chilean game show, early VR tours, the world’s hotel photography rails—and an exit a year before COVID cratered hospitality. Today he’s developing his book into a streaming series and thinking hard about how AI will reshape production.

It started with Pac-Man (and a pocketful of quarters)

• Be your own customer. In college, Henry was killing time at a laundromat, craving Pac-Man. No machines. He cold-called every laundromat in Tucson, found interest, bought used cabinets at auction with tuition money, and placed them.

• Distribution is a strategy. Captive audience, idle minutes, quarters already on hand—perfect unit economics. Rotate under-performing cabinets; rinse and repeat.

• Lesson: “If it’s your problem, it’s probably someone else’s too. Ask. Try. Place a small bet.”

Start at the bottom, learn the stack

• Henry moved to L.A., joined a travel film crew as a production assistant, worked up through sound, AD, and producer.

• Why it matters: founders who’ve worn multiple hats manage better—because they understand how the pieces fit and what “good” looks like at each layer.

Stack opportunities, not just skills

• Chile pivot: After years filming in Latin America, Henry noticed fresh demand: a dictatorship ended, new TV stations needed content. He pitched a youth game show (Machos), partnered locally, and shipped.

• VR tours → infrastructure: A 360° demo sparked World Travel Vision. Hotels asked, “How do we put this on the web?” That revealed a bigger gap: standardized photo distribution for Expedia/Orbitz et al. Twenty-two years later, most hotel photos you see online rode rails his company built.

• Exit discipline: He carried a “number on the mirror” for a decade. When a buyer met it, he sold—60 days, no banker—one year before COVID. Luck favors calendars with clear targets.

“You have to be prepared and lucky. You keep planting seeds, and you’re ready when timing shows up.”

Money: respect it like it’s yours (because it is)

• Bootstrapping teaches unit economics and frugality.

• Raising too early can turn founders into fundraisers instead of builders.

• Knowing your enough—and sticking to it—lets you make unemotional decisions when the offer comes.

The next act: a paranormal love story—and a series

• The book: The Reincarnation of Marie (based on a real 19th-century diarist whose journal became a bestseller after her death). A young man reads it 70 years later, falls for the voice on the page, then finds her reincarnation.

• The series: Working title “Slippin’”—a time-slipping tapestry of past lives, karmic debts, and present-day consequences. Theme: Does love transcend time?

• Plan: Henry prefers traditional production—but is pragmatic: if traction stalls, AI text-to-video may become the fastest, most economical path.

AI will remake film & TV (sooner than we think)

• Cost + speed compression: Text-to-video and asset libraries will let streamers produce multiple series for the price of one, and deliver season two in months, not years.

• A-listers vs. “synthetics”: Top stars keep leverage; everyone else risks being replaced by blended likenesses with clean IP. New actors signing away likeness rights today may regret it tomorrow.

• Format shift: Expect more short-form arcs (6–10 minutes) with strong hooks, optimized for phones and attention windows.

• Culture fragmenting: Hyper-personalized content threatens shared “we all watched it” moments; social discovery will need reinvention.

Founder lessons you can use tomorrow

Opportunity Pattern (repeatable):

1. I have this problem.

2. Others here likely have it too.

3. Can I test a solution this week? (low-cost pilot, real users, fast feedback)

4. Where’s the distribution? (captive audience, partners, platforms)

5. What’s the bigger system gap? (infra beats single features)

Exit Readiness:

• Know your number and why.

• Keep clean financials and key metrics.

• Build options (pipeline, partners, plan B), so you’re never selling from fear.

Creative + AI Reality Check:

• Crawl: previz, boards, lookbooks, casting explorations, trailer experiments.

• Walk: background plates, crowd scenes, pickups, localization.

• Run: episode-level synthesis where IP is clear and audience signal is strong.

• Keep human taste in the loop. Ship faster, not lazier.

Advice to his younger self

“Enjoy the ride. Don’t pre-grieve problems that may never happen. Manage stress—walk, meditate, step out of your head.”

Pull quotes

“Why not me?”
“If you’re scanning for opportunity, you need to be prepared and lucky.”
“Streaming economics will favor series that are cheaper, faster—and still good.”
“Contracts last longer than hype. Read the likeness clause.”

My take

Henry’s story is a masterclass in opportunity stacking: notice a local need, run a small test, then follow the plumbing to where the real value lives. His take on AI is refreshingly practical—optimistic about speed and cost, sober about IP and careers. The through-line: do the simple thing now, and be ready when luck knocks.

Credits

Recorded for Interchain.me. Host: Roberto Capodieci. Guest: Henry Woodman.

Explore

• Book & series hub: mariethestory.com (details on The Reincarnation of Marie and the “Slippin’” series).

• Henry’s updates and production news: see the site above; we’ll link key items in the show notes.