Show Notes
Funding stage: Pre-seed. The only public round is Antler's roughly $180K Pre-Seed check in December 2022, with no priced seed round disclosed.
Did you know that winning a lawsuit can be a worse bet than a Vegas table?
Morgan “Mo” Duffy Tregenza thinks so, and she has the courtroom miles to back it up.
Mo grew up in Telluride, Colorado, the daughter of a zoologist, back when mining and ranching families still shaped the town. She's an attorney by training. Her grandfather spent 30 years as a judge, then became a mediator in retirement. He taught her that people stand behind outcomes they help build.
Mo figured out early that she had no interest in tearing the other side apart. So she stood in Denver County courts asking judges to hand her cases to mediate. Today she's the founder and CEO of Levelheaded, a Denver company pairing certified mediators with Keel, its AI resolution engine, on a mission to make the world less litigious.
Ryan Estes and Mo dig into why the US legal system runs like the world's priciest group therapy. By Mo's count, about 97% of cases never reach trial, and winners collect only about one time in five. That's why she tells friends to skip the lawsuit and take the vacation.
The heart of the conversation is how great mediators work. Rapport comes before anything else. People get space to vent. Then comes looping: repeating back what you heard, in neutral words, until you see someone put down the sword.
Mo covers the practical side of settling, too: why the fight is rarely about the broken contract, why the first offer is almost always the best one, and why both sides have to walk in knowing what they'll give up.
She also shares the story of two rural Colorado neighbors whose decades-long feud ended with an annual Christmas tree, plus the glass of water lesson every founder should tape to their monitor.
Then the conversation turns to AI agents. Ryan is building an autonomous agent and obsessing over her personality. Mo breaks down the mediator traits that belong in agent design: honesty without cruelty, process discipline, curiosity, and the humility to admit a mistake the moment it's caught.
They also explore why AI org charts will need an AI mediator, and why agents built by different companies will need a referee. Mo describes a Zoom plugin idea that drafts the agreement before the call ends.
If you're scaling a startup with AI, or quietly dreading a co-founder conversation, this one will help you put the glass down.
Q&A: What Founders Ask After This Episode
How do I handle a co-founder breakup without going to court?
Bring in a neutral mediator early. Mo compares a co-founder split to a divorce, because you're tied together legally in many ways, which gives both of you strong reasons to agree. A mediator lets both sides be heard, surfaces the real grievance, and helps you trade from a list of must-haves and give-ups.
Is it ever worth suing a contractor or vendor?
Rarely, by Mo's math. She estimates roughly 97% of cases settle before trial, and winners have about a 20% chance of collecting. Wage garnishment is slow and small. Her advice is to count the years of stress, not just the dollar amount, and look for the earliest off-ramp.
How do I de-escalate someone who is furious with me?
Build rapport first. Put the phone away, give them room to vent, and loop their words back neutrally. Watch for the moment their demeanor shifts, when they “put down the sword.” That's when people become open to creative problem solving.
When should I make or accept a settlement offer?
Early. Mo says the earliest offers in a negotiation are almost always more generous than the ones made close to a court date. Go in knowing what you won't move on and what you can give up, and expect movement from both sides.
What personality should I give my AI agent?
Borrow from great mediators. You want honesty without being a jerk, a clear process, curiosity about the outcome, and the humility to admit an error the moment it's caught. Mo says an AI owning a mistake wins her trust faster than flattery ever could. Avoid people-pleasing agents that agree with everything.
Do AI agents need conflict resolution built in?
Mo thinks so. As agents gain autonomy, you need signals that flag when something is going sideways, plus clear moments where a human can pause or step in. Once your agents start negotiating with other companies' agents, the incentives won't line up, and an AI mediator becomes the referee.
Where does AI help mediation, and where do humans still matter?
AI can take the notes so the mediator stays fully present, organize the facts, and draft the agreement. Levelheaded still keeps humans in the loop on most cases. Mo is watching closely for the point where removing humans starts to hurt resolution durability.
URLs Mentioned in the Episode
- Levelheadedhttps://belevelheaded.com
Mo's Denver dispute resolution company, pairing certified mediators with its AI resolution engine, Keel.
- Email Mo directlymailto:morgan@belevelheaded.com
Reach this episode's guest directly.
- 1% for the Planethttps://www.onepercentfortheplanet.org
The nonprofit whose members give 1% of sales or income to environmental groups.
- Ryan Estes on LinkedInhttps://www.linkedin.com/in/estesryan/
Connect with the host.
- AI for Foundershttps://aiforfounders.co
The newsletter and podcast this episode comes from.
- Inbox Alchemyhttps://inboxalchemy.co/
Ryan's tool for building a newsletter audience you own instead of renting from a platform.
- CEOfriendhttps://bit.ly/3SrjgL1
Free competitor analysis from this episode's AI advisory board sponsor.
- AI Native Studenthttps://ainativestudent.com/
AI skills training for job seekers, this episode's sponsor.
- Momentoushttps://crrnt.app/MOME/8RDrnXDd
35% off any supplement subscription, this episode's sponsor.
- Taelorhttps://taelor.style/
An AI men's fashion stylist and this episode's sponsor; use code RYAN30 for $30 off.
- Get Howdihttps://gethowdi.com/
An autonomous AI sponsorship agent for podcasts, this episode's sponsor.
Named Frameworks
The Glass of Water Rule
Why the weight of a dispute is about time, not size.
- →A problem is light to hold for a minute and impossible to hold for a day. The weight never changes, you do.
- →Every month you carry a dispute compounds the stress.
- →Decide early whether this problem is worth years of your life.
Rapport Before Resolution
The first move in any mediation.
- →Connection comes first, even when both sides arrive hot.
- →Give people room to vent the parts that hurt.
- →Stay fully present: no phone, no note taking if a tool can handle it.
- →Wait for the “sword down” moment before moving to solutions.
Looping
The de-escalation technique underneath everything else.
- →Repeat back what you heard in the most neutral way possible.
- →Use their words, not yours.
- →Keep going until they feel heard.
The Off-Ramp Ladder
Why timing an offer matters more than its size.
- →Every dispute has off-ramps between “I have a problem” and “we're in front of a judge.”
- →The further down the road you go, the riskier each off-ramp gets, and the road ends at a cliff.
- →The earliest offer is usually the most generous.
The Give-and-Take Ledger
How to walk into a negotiation ready to move.
- →List what you feel most strongly about and what you're willing to trade.
- →Come in ready to move, even if you have to dig deep to find something to give.
- →Expect to get a little uncomfortable, and possibly something different from what you walked in wanting.
The 18th Camel
The hidden interest that unlocks a deal.
- →The name comes from a mediation parable about an inheritance of 17 camels that can't be split until someone lends an 18th.
- →Mo uses it for the outlying interest that becomes the crux of the whole deal.
- →It could be a stapler, a Christmas tree, or a painting on a wall. Find it and the balance sheet gets easy.
Remember When It Worked
The common ground an offer gets built on.
- →Most conflicts start from a relationship that once functioned.
- →Remind both sides what each wanted from the other at the start.
- →Treat the negotiation as an exchange, and ask everyone to act respectfully.
The Read-It-Aloud Test
A gut check before hitting send.
- →People fire off texts and emails they'd never say in person.
- →Ask, “Would you read this out loud with the other party in the room?”
- →Most people immediately soften.
The AI Mediator in the Org Chart
Where agent design meets conflict resolution.
- →AI org charts need a rapport-first agent to handle conflict between personalities.
- →Build signals that flag when an agent is going rogue.
- →Define clear moments where humans can pause or step in.
- →Plan for the day your agents negotiate with someone else's agents.
Glossary
Mediation
A structured conversation, guided by a neutral third party, where the people in a dispute build their own agreement.
Certified mediator
A trained neutral who guides mediations. At Levelheaded, every agreement is approved by a certified mediator.
Keel
Levelheaded's AI resolution engine. It organizes the facts, surfaces mutual terms, and hands hard cases to a human mediator.
Looping
Mediation technique of repeating back what a party said, neutrally, so they know they've been heard.
Rapport
The trust and connection a mediator builds with each party before problem solving begins.
Neutral
A mediator's stance of not taking sides.
Stipulation
A written agreement between parties, often filed with a court, that records how a dispute was settled.
Settlement
A resolution the parties agree to before a court decides.
Litigation
Resolving a dispute through the court system.
Garnishment
A court-ordered process that takes part of a debtor's wages to pay a judgment.
Appeal
A request for a higher court to review a lower court's decision.
Online dispute resolution (ODR)
Resolving disputes through digital platforms instead of in person.
ICODR
International Council for Online Dispute Resolution. It publishes ODR standards that Levelheaded self-certifies against.
18th camel
A mediation metaphor for the creative or hidden interest that unlocks an agreement.
Human in the loop
A system design where people review or approve what AI produces.
AI agent
Software that can take actions toward a goal with some autonomy.
AI org chart
A company structure where AI agents fill executive and manager roles and route tasks to humans.
Sycophancy
An AI's tendency to flatter or agree with users regardless of accuracy.
NPS (Net Promoter Score)
A customer loyalty metric. Levelheaded reports a score of 70.
Pre-Seed
The earliest institutional funding stage, often from an accelerator or angels.
