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Best of Founder Mode II · Founder Mode

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  Welcome back to Founder Mode. One thing we've learned doing
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  this show 40 Times Now is that the same problems keep showing
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  up, just in different clothes, different industries, different
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  stages, different personalities. But the pressure is the same.
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  Yeah. You're trying to make decisions
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  with incomplete information, limited time and real
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  consequences. What actually helps isn't
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  another framework. It's hearing how other builders
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  think when things get messy. So what you're about to hear are
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  the moments where people stopped posturing and just talked about
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  what worked and what didn't, and what they do differently.
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  If some here makes you uncomfortable, that's probably
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  the point. Healthcare exposes bad
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  assumptions fast. Yeah, Rebecca has lived inside
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  real implementations. Not demos, not decks.
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  She explains. Why Go live isn't the end of the
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  work. It's where the real learning
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  begins. Well, one.
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  It's the theory that people think that go.
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  Live is the finish line like go, live is not.
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  The finish line. Go live is when you actually.
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  Get to. Do the testing and so that's.
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  Where you create a. Bottleneck is that you are like,
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  we're good. We've gone through one week of.
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  Go live. Everything's working.
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  We don't. Need to make.
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  Any more changes? But that's actually.
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  Where the magic happens is through that go live.
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  A lot of teams fail for reasons that never show up in a road
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  map, Anurag argues. We don't just teach the most
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  basic relationship skills and then we're surprised when things
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  break. Yeah, this is one of those ideas
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  that sounds obvious once you hear it.
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  I mean, it's a huge thing, right?
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  And I think we are doing a very ill service to the boys in our
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  community, in our in our society where we're not pushing them,
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  we're not empowering them to go take risk.
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  You know, like I was just talking to my wife actually
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  yesterday and I'm like, I don't understand why in school there
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  isn't a course on interpersonal effectiveness.
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  So I'll give an example. Dialect of behavioral therapy
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  was one of the very popular therapeutic modality has a has a
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  section called interpersonal effectiveness and it literally
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  teaches frameworks on how to build relationships.
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  So for example, there's a skill called the give skill.
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  It sounds for be gentle, act interested, validate and use an
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  easy manner. I can guarantee you in every
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  single interaction, if you use this with your wife, with your
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  kids or your spouses, it will exponentially increase the
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  quality relationship. There's a temptation right now
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  to add AI everywhere. Yeah, John tells a story about
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  what happens when you do that before you've earned user trust.
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  It's a lesson a lot of founders learn the hard way.
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  I've got a pretty good, a very good friend, a very close friend
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  who I spent, you know, a couple hours one day really trying to
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  talk him out of the new direction for his business.
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  Not a new feature. OK, This was like, when users
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  log into my thing, they're going to see this now instead.
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  And I was like, dude, please, man, you this, this like isn't
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  right. Like, why don't you try, Why
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  don't you try a little bubble to see if they want to use it pop
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  up a little bubble. Do you want to try this feature
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  and do some kind of like super scaled down version of it?
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  He so this is a few weeks ago. He launched this just a couple
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  weeks ago. Users didn't like it, they
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  didn't trust it. The feedback came in.
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  I you know, I don't like AIAI is dumb, right?
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  He's not building for tech founders, right?
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  He's he's got like ordinary people as his users.
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  And so it's, it's gone. This, this feature he spent a
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  couple weeks building it no longer exists.
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  The new direction for his business looks a lot like the
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  old direction of his business now.
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  So I, I, I would do, I would do a lot more research, talk to
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  your customers before you, before you try to fly.
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  This is one of my favourites. This company got acquired after
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  we interviewed him. I got to think we had something
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  to do with that. Pricing feels very simple when a
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  category is young. Scott explains why it gets
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  harder over time, and why usage ends up being the only signal
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  that really this reframes how you think about value.
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  The main thing I would just say is complexity increases as
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  industries age. That's like my main prediction.
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  And I do think the good thing about usage is that there's
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  nothing really more fine grained than that that I can think of.
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  Like outcomes are just a flavour of usage.
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  It's like your outcome is my usage.
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  Like it's not these aren't, these aren't different, they're
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  just the same. And ultimately it kind of
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  redounds to this like stream of things that happened in your
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  product that you and I agree on. And I choose this, I value them
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  at this and you charge me that. And it's like kind of what will
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  that's to me, like the terminus of all this stuff, is that it
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  will all be that and then it will be reconstructed in fancy.
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  Packages founders love a full calendar.
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  Bobby calls that out for what it usually is, avoidance.
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  This is about protecting thinking time before the
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  business outgrows you. Allowing yourself the time to
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  think and actually make yourself better is more important than
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  having a busy calendar. You know, people probably look
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  at the day and we want to back-to-back course with like 6
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  different people. And then you're talking to this
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  guy from the UFC and this guy from a sports agent and you
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  know, you're talking to it. You know, what event can we do?
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  And like you're just being a, you're just being a busy fool.
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  You know, realistically, you know, all those books everyone
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  buys and you never reads, you can be better taking a bit of
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  time to read to one of them. And you never know what might
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  come into your head. So I think like keeping yourself
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  busy enough so you're not itching to get another course.
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  But you know, you definitely need to have time to think us
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  about it because ultimately the business wouldn't be there
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  without you. Everyone says they're AI first.
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  Conker has a test that cuts through the noise.
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  If you can't turn real user pain into learning fast, none of it
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  matters. The most important thing that I
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  like to ask people is if I use your app and I complain, how
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  much effort is it for you to take that complaint and turn it
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  into an eval? And the best teams, it's like
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  one or two clicks. If that the teams that are NGMI,
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  they haven't even thought about the answer to that, right?
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  And so, so I think that's really the goal.
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  Like can you get to a point where it's two clicks from
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  someone complaining to something ending up in your evals?
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  This one's just us. We kept circling back to the
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  same idea. Discipline breaks down in broken
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  systems. Health isn't solo, and neither
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  is work. You've you've come up with this
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  pretty good idea that you've shown me around developing, you
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  know, board of directors for decision making and you have
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  like this board of directors for your health Now talk, talk about
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  how how you've set that up. Yeah.
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  So I mean, again, everybody's got their like, you know,
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  amazing prompt for chat And and I the thing that I stumbled onto
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  this, I'd like somebody had written like this council sort
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  of approach. I was like, oh, that's
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  interesting this council and I was like, oh, it's kind of like
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  a board of directors. And so I was like, well, a board
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  of directors is interesting because like, if you imagine
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  like in a company's sake, they'll have like 5 people,
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  seven people, 13 if it's bigger or whatever.
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  And they each have their own experiences, expertise.
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  And so I was like, well, if I'm thinking about my health, like I
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  want somebody that's interested in like, you know, exercise,
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  somebody that's interested in longevity, somebody that's
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  interested in like cardiac experts for like heart, somebody
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  that's interested in like men's health.
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  Somebody's interested in like all these things and saying
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  like, who would be like a world renowned expert to have on your
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  panel? Private equity often gets
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  caricatured into just cost cutting.
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  Jason looks at it from the operator's chair where outcomes
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  actually get created. AI changes the dynamic when you
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  start with real problems instead of tools.
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  AI has turned that on its head and say let's look at your
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  problems and let's help you solve the problems the way that
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  you already know how to do them and do it faster, do it better,
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  do it cheaper, do it, do it in a way that actually helps create
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  more win wins for you and for your customers.
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  Shipping AI inside an enterprise is a different game, especially
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  one as large as Microsoft. Yeah, Sonia talks about the gap
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  between impressive demos and systems people will trust with
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  core workflows. Governance ends up being the
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  unlock. What we learned was it
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  ultimately it it, it ended up being one of our key
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  differentiation. What we learned was if you give
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  enough governance and control and transparency around it, it
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  was actually actually helped the RPA developers to actually adopt
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  it. Consumers recalibrate faster
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  than founders expect. My buddy Max Instacart Co
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  founder, explains how magic turns into table stakes.
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  Your customers are also consumers and they are using
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  ChatGPT, Gemini and all the other, you know, AI assistants
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  that are, that are out there. And so they're getting used to
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  having these magical experiences.
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  So it's becoming actually just table stakes for you to have
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  these kind of magical experiences in your product too.
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  Building software has never been cheaper, Natalie argues.
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  That doesn't make it easier. It shifts where the real
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  difficulty actually lives. The biggest issue is
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  understanding what the client wants, because often times the
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  clients don't know themselves what they want, right?
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  So being able to clearly understand the problem and
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  clearly articulate the solution is the biggest value, for
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  instance, that Jet Rockets brings to its clients, right?
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  So I think that yes, absolutely we're going to use Lovable and
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  Droplet like other tools to generate commodity apps that,
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  you know, sort of like input in output, you know, data in, data
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  out, Something very basic, maybe like, I don't know, like a wish
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  list registry for your wedding, you know, that you want to send
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  to your friends and family instead of using something
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  online and stuff like that. Something very basic, simple,
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  that does not require a whole lot of thinking, processing, you
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  know, what if scenarios, etcetera.
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  The moment things get a little bit more complex, AI is so far
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  away from even like getting anything done right now.
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  Decarbonization conversations usually jump straight into the
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  end state. Kevin explains why hybrid
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  aviation is the bridge that actually earns trust.
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  It's like these expanding horizons where hybrid is a
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  bridge into the fully electric opportunities of the future.
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  And you better believe that those operators who are flying
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  the 100 mile hybrid electrics today are probably going to rely
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  on the trusted brands that they already know in electrification
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  when they go and switch to fully electric.
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  And that's the position that Amber is taking, which is start
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  with electrification, build trust, and then whenever battery
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  technology and infrastructure makes sense, we can transition
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  over to fully electric for those customers too.
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  Most conference booths disappear into the background.
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  We tried to do the opposite and then actually measured whether
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  it worked. We did the math.
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  Like 10 to 20% of all conference attendees came to our booth.
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  Well, not just scanned it, like actually they scanned their
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  badge. So So going back to my question,
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  what's the goal? To build relationships, get new
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  business, grow the business, get new customers.
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  You've already integrated with this platform, right?
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  Yeah. Healthcare moves slowly until it
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  doesn't. Max points to where adoption
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  exploded because the pain was undeniable.
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  So AI scribes have been the fastest adopted technology in
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  the history of healthcare period.
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  Health systems and healthcare in general have really long sales
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  cycles. Those have basically been cut in
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  half. In AI, McKinsey just put out a
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  report last week, the state of AI 2025 Healthcare is like third
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  or fourth in terms of agentic adoption in general AI adoption.
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  And before that, Menlo Ventures put out a report a couple weeks
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  ago that Healthcare is well above average, the industry
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  average across all industries in terms of adoption.
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  Health systems are leading the pack there because they have
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  these real problems with provider burnout.
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  So you see the scribes getting adopted, RCM collecting that
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  dollar I spoke about earlier. They're doing real things, like
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  it's not just hype, like maybe the valuations and some of that
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  causes folks to to go to that thought, but there's real stuff
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  happening in a lot of transformative companies too.
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  Most founders default to venture because it's familiar.
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  Tim explains why that habit quietly erodes ownership.
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  I think a lot of founders really just leave that on the table and
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  it's money. That's set aside because it's.
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  Just such a pain to get to it so they just go after the next VC
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  round and keep stacking on dilutive.
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  These are. Capital intensive businesses.
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  So this founders are exiting with a sliver of their company
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  left. We talk a lot about focus.
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  Austin is building something that forces the issue through
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  design. Yeah, we sell more than just a
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  phone. We're selling the real life
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  back, whether that's connections in one way or another.
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  And for us in our online community, we're trying to bring
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  people together who are all on this journey of trying to
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  achieve their goals in our phones is the mean for helping
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  with that goal. And for us, that is a community
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  like a lot of minimal phones, it could be a very lonely
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  experience because you think you're and it alone.
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  And for us, we're trying to put them together and bring people
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  together and bring ideas together and make everyone feel
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  supported and a part of OK. I'm not doing this alone.
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  Aviation doesn't forgive sloppy decisions.
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  Max explains why stress and judgement don't mix.
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  If you have way too. Many stresses you know you've.
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  Got. Some of the life, you know, kind
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  of thing going on changing job or divorce or get any of those
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  major kinds of things. That's not the time to go fly
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  because that's too much dress that you won't focus on, but
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  things that you need to. Do.
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  Unlimited sounds pretty generous.
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  Jonathan breaks down why it's really a math problem.
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  It was almost like it's like a gym membership where there's a
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  couple of meatheads that should that are there all the time.
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  And then I have a membership I should go more often.
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  And they you kind of bank on the fact that no, not everybody
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  shows up at once. If you want to learn fast,
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  remove the safety Nets. Racer Allen explains why raw
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  environments teach faster. The Formula car is the most is
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  the best platform to be able to learn from because of the fact
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  that it is there is no traction. Control.
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  It's just you're just you in the car.
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  And the the correct technique, there's specific technique to
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  driving a car that needs to be covered off and what you can
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  learn in our school and formula cars apply to other different
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  types of cars. If there's a through line in all
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  of this, it's not about AI, healthcare pricing, or flying
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  planes. It's about learning how to make
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  calls when there isn't a right answer, where to push, when to
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  wait, when to walk away from something that looks good on
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  paper, and when to trust yourself enough to keep going.
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  Anyway, if one of these moments stuck with you, go listen to the
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  full conversation. And if Founder Mode has been
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  useful to you, do us a favor. Subscribe, leave a review, and
• 14:39
  share it with someone else who's building.
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  It helps more than you think. And that's it for today.
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  Remember, demos don't matter, production does.
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  We'll see you next time on Founder Mode.