This was my first live recording, and it exceeded every expectation I had for what this show could be.
Huge thanks to Jenna Birch and the SISU team for co-hosting the event. (If your startup or fund needs creative communications or media strategy, check out sisubrandpr.com — they’re pros.)
The conversation paired Cyan Banister, co-founder and GP at Long Journey Ventures, with Cristian Cibils Bernardes, co-founder and CEO of Autograph, an AI “personal historian” that captures family stories through voice interviews with an agent coincidentally named Walter.
If you don’t believe in synchronicity, you will by the end of this episode.
Cristian’s childhood email address included Cyan’s name. A database he spun up after raising his seed round was randomly tagged “cyan.” Cristian’s grandmother and Cyan share a birthday, among other eerily parallel life events. As I said in the room, “it sounds like quantum entanglement.”
What unfolded was part strategy session, part metaphysical collision, and 100 percent useful. Here are two tactical ideas worth stealing:
1. Ask yourself Cyan’s new diligence question: “What’s your higher calling?”
She’s cut résumés and metrics from her early-stage screens. Now she starts every founder meeting with a simple line:
“You’re smart enough to do anything — why this?”
She’s looking for founders who already know what they’ll do when the money shows up, people who treat success as stewardship, not a jackpot. If you can’t articulate your higher calling, leave your phone at your desk and think it over while you get some fresh air.
2. Practice Cristian’s ‘two-questions-deep’ listening.
His company depends on memory, but the tactic works anywhere: go two questions deeper than feels natural. It’s even baked into how their Walter interacts with Autograph users.
“How did that make you feel?”
“What period in your life does that remind you of?”
Most founders stop after the first answer; the best ones pause and listen for what comes next.
Cyan and Cristian both offered thoughtful answers to my final question: if you were looking for a job at an early-stage startup, what’s one question the CEO would have to answer before you could take the offer? (You’ll want to hear both.)
Thanks again to Cristian, Cyan, Jenna Birch and Team SISU, and everyone who attended!
Listen to the full live episode on Apple Podcasts, Spotify, or wherever you get your shows.
— Walter.
Apple Podcasts
Spotify
RUNTIME 47:19
EPISODE BREAKDOWN
(1:54) Why Cristian named Autograph’s AI agent “Walter.”
(3:37) When they connected, Cristian saw “a bunch of synchronicities along the way that just kept pointing in this direction.”
(4:59) Cyan: “When he showed up and we were sitting together having coffee, I immediately was like, ‘yes.’”
(6:03) The sheer number of coincidences linking these two is unsettling — “quantum entanglement” comes to mind.
(8:18) Cristian and Cyan share their non-consensus takes on consumer AI.
(10:53) Cyan describes the framework she’s using to assess early signals as an investor.
(12:51) “I will not look at your résumé. I won’t look at what you did. Whatever you tell me in that interview is what I’m going to go off of.”
(14:42) “Fundraising is grueling. It was 50 conversations before I met Cyan, and then I had, I think, another 30.”
(16:53) Cyan’s framework for backing vs. passing.
(18:26) The three essential ingredients Long Journey Ventures seeks in founders.
(22:00) What a “magically weird” founder looks like — and why they’re so valuable.
(26:15) A red flag that ensures you won’t get a second meeting with Cyan.
(27:52) A behavior that virtually guarantees a second meeting.
(29:45) Cristian describes Autograph’s moat.
(34:40) “This whole thing doesn’t work if the trust element isn’t there.”
(38:08) What founder-investor fit looks like in their working relationship.
(41:57) One experiment founders should run this week.
(43:10) The most underrated founder superpower.
(44:10) “If you were interviewing for a job at an early-stage startup, what’s one question you’d have to ask the CEO before you could take the offer?”