If Possible

If Anything Were Possible

Colleen Cook & Scott Williams — Mon, 02 Nov 2026 00:55:51 GMT

A few times this season, we've left you with one question. In the Season 1 finale, Colleen tells where it came from: a nonprofit whose dreams always came with the limits built in.

Colleen Cook and Scott Williams on why AI is the great equalizer for nonprofits. For-profits will use it to do more with fewer people; nonprofits never had enough people to begin with. Why this is the best time ever to be a nonprofit, even on a small budget. The telephone operator who is so much more than a telephone operator. What changes when a nonprofit builds the right system, and why your North Star might be closer than you think. Plus a 2000s boy band, a sponsor that does not exist, and If Possible Theater: Three Wishes.

Chapters
00:00 Cold open: a spaceship
00:28 1. Where the Name Came From
04:05 Song: it's a beautiful place, baby
04:27 2. The Best Time Ever
09:44 3. Telephone Operators
13:20 A fake sponsor
13:55 4. With the Right System
17:06 If Possible Theater: Three Wishes
18:07 5. We Got a Spaceship
22:11 One last question

That's Season 1. If someone sent you straight to the finale, start at Episode 1: Too Busy for AI. Follow If Possible wherever you're listening so Season 2 lands in your feed.

Follow If Possible
Spotify: https://open.spotify.com/show/3TmyOfF5gliAKO3rmeIOal
Apple Podcasts: https://podcasts.apple.com/podcast/id6818487795
YouTube: https://www.youtube.com/@ifpossibleai
Instagram: https://www.instagram.com/ifpossible.ai/
Colleen on Instagram: https://www.instagram.com/if.colleen/
Scott on Instagram: https://www.instagram.com/if.scott/
TikTok: https://www.tiktok.com/@ifpossible.ai
The If Possible Newsletter, free every Wednesday: https://ifpossible.ai/newsletter
Work with us: https://ifpossible.ai/work-with-us
Say hi: hi@ifpossible.ai

If Possible: AI coaching and implementation for ambitious nonprofit leaders. https://ifpossible.ai

One more note for the end of the season: every idea and nearly every voice you heard this season was ours, and AI did most of the editing inside a process we built on close to 3,000 yes-or-no decisions about how If Possible should look and sound. Nothing aired in the order it was said, which is what editing has always been. If you want your nonprofit to have something like this, give us a shot.

Fundraising Is Fear

Colleen Cook & Scott Williams — Mon, 02 Nov 2026 00:55:21 GMT

Colleen's first development job started with a front-page story saying her organization would close, and every donor in town mad at them. Years later she has a word for what sits underneath every hard ask: fear.

Fear of harming a relationship, fear of a no, fear of walking in without knowing the person. Colleen Cook and Scott Williams talk about what turns that fear into confidence: the color of a relationship that nobody ever tracks, an Olympian who writes "Dad" inside her spikes, a Chicago Bulls mug, one coffee with one donor and the robotics competition on the 15th, and a nonprofit that found 5,000 prospects in its own data and finally said "we're ready to fundraise." Plus a 90s R&B slow jam, a sponsor that does not exist, and If Possible Theater: The Big House on Maple Street.

Chapters
00:00 Cold open: every donor in town
00:37 1. Every Donor in Town
03:58 Song: mad at us, baby
04:23 2. Fundraising Is Fear
07:26 3. Dad, Inside the Spikes
11:35 A word from our sponsor (it isn't real)
12:10 4. One Coffee, One Donor
17:38 If Possible Theater: The Big House on Maple Street
18:44 5. Ready to Fundraise
22:41 The question we'll leave you with

Up next, the Season 1 finale, Episode 10: If Anything Were Possible. Where the question behind the name came from.

If Possible: AI coaching and implementation for ambitious nonprofit leaders. https://ifpossible.ai

A quick note for the curious: the people, the stories and almost every voice in this episode are real, and AI did most of the editing inside a system built on close to 3,000 small yes-or-no decisions about how we want to sound. Anyone can use AI for anything; we chose to use it for story. If your nonprofit wants to do the same, we'd love to help.

The Bathroom Sink

Colleen Cook & Scott Williams — Mon, 02 Nov 2026 00:54:55 GMT

Most of what we build with AI is half done for a while, like the 13-inch discount sink we lived with in our unfinished office kitchen: functional, and not where you want to live.

Colleen Cook and Scott Williams on the honest middle of AI for nonprofits. Why their job is to fail a whole bunch of times so you don't have to. The startup years, the maze of dead ends, and the report Colleen finally just turned off. The AI button inside the software your nonprofit already uses, and why the report numbers look the way they do. The steam engine story, and what nonprofits can learn from how factories finally got electricity right. And the day you can leave the room. Plus a 1960s soul girl-group song, a sponsor that does not exist, and If Possible Theater: First on the Block.

Chapters
00:00 Cold open: the 13 inch sink
00:42 1. The Bathroom Sink
02:53 Song: a bathroom sink in the kitchen
03:16 2. We Broke It Every Way
06:14 A word from our sponsor (it isn't real)
06:48 3. The AI Button
08:57 If Possible Theater: First on the Block
09:58 4. The Steam Engine
12:40 5. Then I Leave the Room

Up next, Episode 9: Fundraising Is Fear. The honest reason asking feels so hard.

If Possible: AI coaching and implementation for ambitious nonprofit leaders. https://ifpossible.ai

How this one came together: the two of us talked for hours, and AI helped us find the part worth your time. Every idea and nearly every voice is ours, and the cuts, the music and the jokes ran through a process built on thousands of yes-or-no calls we made on purpose. If you'd like something like this for your nonprofit, we'd love to help.

Whatever's in Your Head

Colleen Cook & Scott Williams — Mon, 02 Nov 2026 00:54:33 GMT

Colleen and Scott spent years running an agency that built websites, so they know what it costs to hand-code an idea. Then AI started handing them clickable web pages in minutes.

Colleen Cook and Scott Williams on the AI output almost nobody is using yet. Why whatever is in your head can now be something your team can see, click and use. How one page sent from vacation launched a whole marketing campaign with a 30-minute stand-up. Why Scott, at fourteen, had songs and no guitar, and what that has to do with strategists today. The cat shelter software nobody will ever sell you, and why you never have to "lump it" with software again. Plus a country song, a sponsor that does not exist, and If Possible Theater: The Picture Box.

Chapters
00:00 Cold open: songs in my head
00:41 1. Whatever's in Your Head
04:15 Song: now you can see it
04:37 2. Launched From Vacation
10:04 A word from our sponsor (it isn't real)
10:37 3. Songs Without a Guitar
15:12 If Possible Theater: The Picture Box
16:16 4. Software Nobody Will Sell You
20:30 5. You Don't Have to Lump It
25:20 The question we'll leave you with

Up next, Episode 8: The Bathroom Sink. The honest episode, and a 13-inch sink.

If Possible: AI coaching and implementation for ambitious nonprofit leaders. https://ifpossible.ai

This show is produced with a lot of help from AI, inside a design system Scott has made close to 3,000 decisions on. The ideas, the stories and 99% of the voices are human. Curious how it works? We'll show you.

Ninety-One Assets

Colleen Cook & Scott Williams — Mon, 02 Nov 2026 00:53:52 GMT

Last episode, Colleen called her shot: one day to build a nonprofit's whole year-end campaign with AI. Here's how it went.

Colleen Cook turned one recorded strategy conversation into 91 pieces in eight hours: segmented appeal letters and reply cards, a Giving Tuesday push, nurture emails, social, a case video, call scripts, a hub for the whole team, and a card for handwritten thank yous. Scott Williams and Colleen get into why you can't just ask AI to "make me a year-end campaign," what made it possible (the brain, the brand system, the context built before), the eight years Colleen spent dreaming about it, and how to steer AI when you don't have the words yet. Plus a song, a sponsor that does not exist, and If Possible Theater: The Overnight Suit.

Chapters
00:00 Cold open: ninety-one assets in eight hours
00:36 1. Don't Send a Christmas Card
04:27 Song: way too quiet
04:48 2. Closing the Loop
09:59 A word from our sponsor (it isn't real)
10:33 3. Eight Years Dreaming
16:21 If Possible Theater: The Overnight Suit
17:27 4. What Made It Possible
21:41 5. Go Do It All
25:40 The question we'll leave you with

Up next, Episode 7: Whatever's in Your Head. Whatever's in your head, you can now see it.

If Possible: AI coaching and implementation for ambitious nonprofit leaders. https://ifpossible.ai

Yes, AI helped make this. So did two people who care a lot about nonprofits and spent real time teaching it our taste. If you want to build something like this for your organization, we'd love to help.

Call Your Shot

Colleen Cook & Scott Williams — Mon, 02 Nov 2026 00:53:14 GMT

Most nonprofits feel like the best kept secret in town because they only speak up when they have an ask. One appeal letter is never enough. Year-end takes hundreds of touches.

A nonprofit called us two years ago needing a big year-end, and too little came in, too late. Colleen Cook and Scott Williams talk through what they would tell that same nonprofit now: how a giving day gets its energy, why your donors want to be the guide and not the hero, and how one recorded conversation becomes a whole multi-channel campaign. And at the end, Colleen calls her shot: one person, one day, a whole Giving Tuesday campaign built with AI from the start. Plus a song, a sponsor that does not exist, and If Possible Theater: Hello, Neighbor.

Chapters
00:00 Cold open: the best kept secret
00:47 1. Too Little, Too Late
04:32 Song: one letter is not enough
04:52 2. Ask Me Four Times
09:46 A word from our sponsor (it isn't real)
10:21 3. Find the Nugget
14:37 If Possible Theater: Hello, Neighbor!
15:37 4. The Best Kept Secret
21:05 5. One Person, One Day

Up next, Episode 6: Ninety-One Assets. Colleen called her shot. Did she do it?

If Possible: AI coaching and implementation for ambitious nonprofit leaders. https://ifpossible.ai

How this episode came together: Colleen and Scott talked, and AI helped find the story, cut it and score it. None of it aired in the order it was said, which is what editing has always been. If your nonprofit wants a content engine like this, give us a shot.

Meat Proxy

Colleen Cook & Scott Williams — Mon, 02 Nov 2026 00:52:22 GMT

A meat proxy is the person who pastes AI output into Slack or an email without adding anything to it. If you've ever received a five-page summary of a two-line idea, you've met one.

Colleen Cook and Scott Williams get into why AI made our messages longer and how to flip it back: use AI to shrink a message before you send it, keep your brain switched on when AI sounds sure of itself, and save the personal stuff, like a birthday card, for yourself. Plus a word that names the cost of all that reading, and why taste is the human part of the job. We picked up the term meat proxy from the AI world, and we love it. Also inside: a song, a sponsor that does not exist, and If Possible Theater: The Navigator.

Chapters
00:00 Cold open: the birthday card
00:36 1. What a Meat Proxy Is
03:42 Song: you're just a proxy
04:02 2. Six Words, Six Hundred Words
08:28 A word from our sponsor (it isn't real)
09:03 3. Not the Birthday Card
11:50 If Possible Theater: The Navigator
12:45 4. Brain On
18:23 5. Humans Have Taste

Up next, Episode 5: Call Your Shot. Year-end, and why one letter is never enough.

If Possible: AI coaching and implementation for ambitious nonprofit leaders. https://ifpossible.ai

Made with AI, on purpose. Anyone can use AI for anything; the real question is what you choose it for and how well you use it. We chose story, and we'd love to help your team do the same.

Hit Record

Colleen Cook & Scott Williams — Mon, 02 Nov 2026 00:50:24 GMT

Most of what matters at a nonprofit is said out loud, and we keep maybe a tenth of it. Colleen and Scott don't say a word in a meeting until somebody hits record. Here's why.

Scott loses seven seconds of Colleen to a phone call and refuses to write it down. They share where their nightly bots came from: one transcript, twelve bots, each one looking for a single thing. Colleen's AI assistant now catches the promises she makes out loud and never writes down. And Colleen Cook and Scott Williams answer the two questions everyone asks: what if people don't want to be recorded, and is it safe to give this to AI? Plus a song about seven seconds, a sponsor that does not exist, and If Possible Theater: Table Nine.

Chapters
00:00 Cold open: until somebody hits record
00:43 1. The Missing Seven Seconds
06:04 Song: seven seconds
06:31 2. Conversation Is Our API
11:37 A word from our sponsor (it isn't real)
12:09 3. Twelve Bots, One Transcript
17:02 If Possible Theater: Table Nine
18:07 4. There's No Home for That
24:34 5. Just Ask

Up next, Episode 4: Meat Proxy. Why AI made our messages longer, and how to flip it back.

If Possible: AI coaching and implementation for ambitious nonprofit leaders. https://ifpossible.ai

Behind the scenes: we talk, AI helps us shape it, and we say yes or no to every choice along the way. That's a few thousand decisions turned into a system that scales. If your nonprofit could use that kind of help, that's the work we do.

A Goldfish With a Brain

Colleen Cook & Scott Williams — Mon, 02 Nov 2026 00:49:06 GMT

Your AI has the memory of a goldfish, and when it forgets, it won't tell you. You'll just see it in the work.

Colleen Cook and Scott Williams get into why AI output disappoints so many nonprofit teams, and what fixes it: a brain. Scott builds a product calculator for a nonprofit in an afternoon. Colleen explains why a brain works like your medical chart. Why telling AI what you want beats handing it step by step orders. And the advice that sounds backwards until it clicks: for a while, don't ask AI for anything. Only tell it things. Plus a goldfish song, a sponsor that does not exist, and If Possible Theater: The New Hire.

Chapters
00:00 Cold open: it won't tell you it forgot
00:42 1. The Calculator and the Goldfish
03:55 Song: give that goldfish a brain
04:14 2. Ten Minutes
06:57 3. Tell It What You Want
09:53 A word from our sponsor (it isn't real)
10:27 4. Your Brain Is a Medical Chart
14:08 If Possible Theater: The New Hire
15:10 5. Only Tell It Things

Up next, Episode 3: Hit Record. The one AI habit we never skip.

If Possible: AI coaching and implementation for ambitious nonprofit leaders. https://ifpossible.ai

A note on how this was made: every idea and nearly every voice you heard is ours, and AI did most of the editing inside a process we built. Behind it are close to 3,000 yes-or-no decisions on how If Possible should look and sound, made once so they can scale. If you want your nonprofit to have something like this, we can teach you how.

Too Busy for AI

Colleen Cook & Scott Williams — Mon, 02 Nov 2026 00:46:43 GMT

Every fall we hear it from nonprofit leaders: we're slammed, let's talk about AI in January. In our first episode, Colleen and Scott make the case for starting with the work already on your plate.

Colleen Cook and Scott Williams take apart the most common reason nonprofits wait on AI, one long conversation at a time. An executive director turns a day-long board report into a ten-minute job. Eighteen slides come together an hour before a meeting, with zero stress. A county airport project gets approved. And the idea underneath all of it: you still have to do the work, so do the next piece of it differently, and you get two works at once. Plus a song about the moving walkway and our first If Possible Theater, The Bucket Brigade.

Chapters
00:00 Cold open: what is important to you
00:38 1. Let's Talk in January
05:29 Song: the moving walkway
05:52 2. Do the Next Thing Differently
10:46 If Possible Theater: The Bucket Brigade
12:07 3. You're Right on Time
17:39 4. The First Time Is Slow
21:55 5. Two Works at Once

Up next, Episode 2: A Goldfish With a Brain. Your AI has the memory of a goldfish. Here's how to give it a brain.

If Possible: AI coaching and implementation for ambitious nonprofit leaders. https://ifpossible.ai

A small note for the curious: this episode was edited with AI and a lot of human judgment. Every idea came from us, and nearly every word you heard is our real voice. Want to learn the process? Give us a shot.