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Is your SEO ready for AI? Jenna Hannon says probably not · AI for Founders with Ryan Estes

• 0:00
  Welcome back to AI for Founders. I'm your host, Ryan Estes, and
• 0:03
  today's episode is an absolute gem.
• 0:06
  I'm joined by Jenna Hannon, the powerhouse behind Hatter where
• 0:10
  they are revolutionizing SEO for the AI era in what she calls LLM
• 0:15
  Search. We kick things off hot with
• 0:18
  breaking news on Pentagon AI contracts, NVIDIA shifting ties
• 0:22
  with China, and the theater of tech politics that feels more
• 0:25
  like Gandalf VS Saruman then Washington VS Silicon Valley.
• 0:29
  Then Jenna really brings the heat breaking down why Venture
• 0:31
  World is consolidating what services a software really means
• 0:35
  and how bootstrapping can still win in a hype driven market.
• 0:39
  Plus, we dive into how founders can actually show up inside AI
• 0:42
  generated search results and why your next $1,000,000 company
• 0:46
  might start with a kite board, a notebook full of customer pain
• 0:49
  points. If you're building anything with
• 0:51
  traction data or dreams, this ones for you.
• 0:54
  First, some business. This episode is brought to you
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  by Kickcaster, where top founders go to get on top
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• 2:54
  Hey Jenna, thanks so much for coming on the show of.
• 2:58
  Course, happy to be here. Yeah, I can't wait to talk about
• 3:00
  Hatter, but I want to jump into some news first.
• 3:03
  We had kind of some breaking news this week, All right?
• 3:05
  I mean, there's always breaking news by the time this comes out.
• 3:07
  It's probably old news, but let's start with a couple of
• 3:10
  things. One, the, the Pentagon just
• 3:13
  handed out large contracts to a bunch of different AI companies,
• 3:17
  Brock being one of them. So, you know, the, the, the beef
• 3:21
  between Trump and Elon could be all smoke.
• 3:24
  You wonder what they're actually up to.
• 3:26
  And the second thing is the trade restrictions between
• 3:29
  NVIDIA and China were lifted. So again, like Trump talks a
• 3:34
  mean game, but it also seems he's making these back deals to
• 3:37
  make sure to for whatever reason.
• 3:40
  So I'd be interested in your take.
• 3:41
  You know, we have a White House now that is absolutely inundated
• 3:45
  with tech, very tech forward, but also seems to be at war with
• 3:49
  it at the same time. What?
• 3:51
  What's your take on all this? You know, I am, I am a Canadian,
• 3:57
  born and raised, but obviously live, live in the US now and
• 4:00
  I've been here for, for a while. It's been a long time in Silicon
• 4:03
  Valley. My take is the government's
• 4:06
  still getting their, you have their head around tech and
• 4:12
  what's going on. Just the the pace in terms of
• 4:16
  tech development currently is so fast and it's very difficult to
• 4:20
  regulate. So if you look at the difference
• 4:22
  between how US is handling it and Europe is handling it,
• 4:26
  Europe is trying to put a lot of regulation in place, which I
• 4:29
  think is very hard to do and stifling a lot of the industry
• 4:34
  there. US was kind of Trump came in and
• 4:37
  said it seemed like the approach was holds let's figure out
• 4:43
  what's going on. And now he's had maybe a few
• 4:47
  folks whisper in his ear and say hey, we're we're stifling
• 4:50
  progress if we do need to compete on this stage.
• 4:54
  I don't know if I have a comment on the, the, so the trade
• 4:59
  relations between China, yeah, sounds like there's a lot under
• 5:02
  the hood there. Yeah, there's so much you don't
• 5:04
  know. It is, it is interesting,
• 5:06
  particularly between Trump and Elon, who are both absolute
• 5:09
  masters of propaganda and creating and and disseminating
• 5:13
  information through their own personal networks.
• 5:16
  You know, so there is definitely a theater it it kind of feels
• 5:22
  like there are a couple of Wizards on the mountain that are
• 5:24
  fighting each other with lightning bolts and I'm just in
• 5:26
  the Shire looking around being like, what are they up to?
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  I, I can't tell at all, but maybe maybe something a little
• 5:32
  more grounded is, you know, after several years, hard years
• 5:36
  of VC, we're seeing like the the AI hype cycle absolutely
• 5:41
  invigorate venture capital and you're seeing funding rounds and
• 5:44
  valuation rounds now that are astronomical.
• 5:47
  How is that kind of affected you and how does that and this might
• 5:51
  dovetail nicely into kind of your company?
• 5:55
  Yeah, of course. I mean, I've been watching VCA
• 5:59
  lot lately and seeing what's happening in in Venture just
• 6:02
  because what I, you know, I've been in in tech for a long time
• 6:07
  and through several cycles. So you see history repeat
• 6:10
  itself. I think now in VC, we're coming
• 6:13
  out of a hype cycle in a very hot market that's been cooling
• 6:17
  outside of AI and you're seeing a ton of consolidation, which is
• 6:24
  a huge portion of venture dollars is going to the same few
• 6:28
  companies, which I don't think we've seen for a while, which is
• 6:33
  kind of interesting because did you ever read the Angel List
• 6:37
  blog? They have a data scientist that
• 6:38
  wrote the blog for Angel List where he would analyze.
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  I think still today it's 20% of deals go through venture deals
• 6:46
  go through Angel List. So they have a lot of data.
• 6:49
  Yeah, no, I didn't read that. So they and I, I went to their
• 6:54
  conference years ago in this data scientist spoke and he was
• 6:57
  talking about when you analyze venture deals, the industry is
• 7:01
  obviously very power law. Just like a lot of things in
• 7:04
  nature, there are a few outsized winners and then there's a very
• 7:09
  long tail. And what he saw from the data
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  was that it is very difficult to predict who the power law
• 7:17
  winners will be. So one of the best investing
• 7:20
  strategies that you can make is actually being in more deals,
• 7:24
  more diversification. And I think over the last decade
• 7:28
  of knowing several investors that are close friends and, and
• 7:32
  asking them about being in that industry.
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  What a lot of them say to me is the companies I thought were
• 7:39
  going to be the winners in My Portfolio are not the ones that
• 7:43
  are leading the pack. The ones I was most excited
• 7:45
  about and the ones that I, you know, I, I wasn't so sure about.
• 7:50
  As an example of this is like a close friend of an investor who
• 7:54
  was the first check into Canva. And he, he really was like, this
• 7:58
  is AII like I like these founders.
• 8:02
  I like their background. I don't know if this is going to
• 8:05
  work. The market for graphic design
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  software is not huge today. I can't evaluate this as a
• 8:12
  traditional VC and that one didn't really surprise him, $40
• 8:17
  billion company today, very unlikely success story.
• 8:22
  And so when I look at this consolidation, my concern is,
• 8:25
  are we are investors investing for returns or hype currently?
• 8:32
  Because if you're investing for returns, you'd probably find a
• 8:35
  different strategy versus height, maybe a better word
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  against markets where if you have a market that in which
• 8:44
  adventure looks today, where there's the very big funds and
• 8:48
  the big funds, the way the fund math works is you need very
• 8:52
  large outcomes, several very large outcomes to return that
• 8:57
  fund. And so you are only looking for
• 8:59
  these outsized unicorns, which by the nature are very hard to
• 9:04
  find and very high risk. Or on the flip side, you're a
• 9:08
  small fund, in which case in order to raise your next fund,
• 9:11
  you need to share markups, which is not the ideal investing
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  strategy because it means you also need to be in the height
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  deals, which leads to, I think where we are today, a lot of
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  consolidation. So less founders receiving
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  capital, which actually I think in the long term leads to kind
• 9:31
  of a slow down because you have less companies that are
• 9:35
  capitalized even in smaller amounts to start developing new
• 9:41
  go to market approaches, applications, technology.
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  Yeah, it's weird. It's like 2 different schools
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  are emerging. That old guard of like, you
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  know, they have, let's say they're looking for founders
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  with Fang expertise. They're looking for the pedigree
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  of the Princeton's, Harvard's, MIT's, that those guys always
• 9:58
  get big checks. They're looking for monster
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  evaluations. And you just keep on like the
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  runway treadmill forever. And then you have the other
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  side. Maybe this is a little bit more
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  on the canvas side where you have non conventional founder.
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  I mean, she's Aussie, you know, and what a great product, but
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  you have in but you also have 10 with so young.
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  Yeah, so. Young so you're seeing a lot of
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  that now we're founders they're kind of looking at like, hey
• 10:21
  man, we want to turn a Unicorn out of like a a handful team,
• 10:25
  you know, four or five guys gals like let's make this happen.
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  So you see things like seed strapping where they're not
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  looking for big checks, they're looking for small checks and
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  seeing how they can 100X that capital and make things happen
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  immediately, which also seems to like follow the kind of
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  instinctively with the way AI products are really taking off
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  now. You know, the, the, the ones
• 10:46
  that just basically have massive traction early on is where you
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  just hit a button and it works like magic and you don't even
• 10:54
  ask questions. And those products just go
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  absolutely bananas. And they're very small, maybe
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  single use case. And again, just works clearly.
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  So talk a little bit about your company.
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  One, explain it like I'm five. And then two, talk about how
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  you've financed and like how you've made decisions about
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  financing moving forward. Yeah, of course.
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  So our, our company is quite simple.
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  We do, we do SEO and LLM search. So this is how do you get
• 11:25
  organic traffic? How do people find your
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  business? It's a very old industry.
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  It's been around for decades. And the way it's been done for
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  decades hasn't hasn't or the way it's been done has not changed
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  in decades. We're suddenly seeing an
• 11:41
  inflection point where the industry is fundamentally
• 11:44
  changing with how people search. And so you're used to searching
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  on Google and you find a list of search results.
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  Now we're shifting to a world where the output is AI results.
• 11:59
  So for a business, what that means is that you need to show
• 12:02
  up essentially on both. So the inputs are the same.
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  So the way that Google analyzes how to break your business is
• 12:11
  very similar to how an LLM analyzes your business.
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  So it's looking at what information on the web exists
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  about your business to help answer questions about your
• 12:24
  business and also what actual technical code it can read to
• 12:33
  understand your business better. So SEO is still the same
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  fundamental inputs you've got content SEO and technical SEO.
• 12:41
  It's just the the output to your customer is.
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  Different amazing the innovate. Oh, go.
• 12:47
  Ahead. Sorry, my apologies.
• 12:48
  Oh. I was going to say, I was going
• 12:50
  to say the, the innovation that we are doing that makes is
• 12:53
  different is kind of to your point of developing these AI
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  technologies that are are now faster than ever.
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  We are leveraging AI to help teams better execute on SEO.
• 13:09
  So SEO is a lot of work behind the scenes.
• 13:11
  You're developing a lot of content for your website.
• 13:13
  You're doing a lot of optimizations that help you
• 13:15
  rank, and we are building tools through AI to help take that
• 13:23
  manual work and automate it. Amazing.
• 13:26
  Now is there an acronym yet for LLMSSEO?
• 13:30
  Is it LSLLMO or something? Like what?
• 13:34
  What do we got? This is this is the question
• 13:38
  right now. So we we've been joking about
• 13:40
  this internally. So it started as Geo generative
• 13:45
  engine optimization. The market doesn't really like
• 13:48
  that turn because it sounds like Geo, like geography.
• 13:52
  So then there was a moment, a flash moment where it was people
• 13:59
  were rebranding it as AO. And now I think people are
• 14:03
  coming to terms with let's just call it LOL search or AI search.
• 14:08
  Let's just go back to the basics here.
• 14:11
  But yours, every SEO influencer that's in this space, you'll see
• 14:17
  is writing has picked an acronym as trying to push it.
• 14:20
  So now we just have too many acronyms.
• 14:22
  They're trying other ones. Why I Yeah, exactly.
• 14:25
  Which is why I've kind of gone back to the basics with AI and
• 14:29
  LLM search. 11 Let's talk about how you guys financed.
• 14:34
  How did you do you guys raise a round?
• 14:37
  We are, so we, we've been bootstrapped and we're actually
• 14:40
  raising right now, which is why VC is on my mind.
• 14:44
  So we, the way that we run our business is we sell a, a full
• 14:47
  solution. So we sell essentially an SEO or
• 14:51
  AI search service. You are a business, you know,
• 14:55
  you want to get more organic traffic.
• 14:57
  You're starting to see that traffic slowed down due to the
• 15:01
  changes that's happening on Google from search to LLM
• 15:05
  traffic, and you want to make sure that you're showing up in
• 15:07
  those LLMS. So we still sell as as
• 15:10
  essentially a service package. And then the difference is in
• 15:14
  our delivery we're giving a tech enabled service.
• 15:16
  So that customer is getting a real time dashboard.
• 15:20
  They can monitor their their performance, our our performance
• 15:24
  real time. They can log in at any time.
• 15:26
  We give them tools to help us with the SEO.
• 15:29
  So if they want to edit content, for example, so if we're
• 15:34
  providing content and they want to pop in there and review it,
• 15:37
  we have a full editor that we provide to them and then we give
• 15:40
  them full visibility. So I think the biggest thing
• 15:42
  that we found in going into the SEO market is when we talked to
• 15:46
  companies about their SEO agencies, they felt like it was
• 15:48
  a black box. We don't really know what our
• 15:51
  SEO agency is doing. We hope it's helping.
• 15:55
  So what the the difference that where you're building is, we can
• 15:58
  take technology and we can show you exactly what's happening on
• 16:01
  the back end. Every single technical
• 16:03
  optimization we're making, every piece of content and how that's
• 16:06
  translating into performance in terms of inbound customers.
• 16:12
  Amazing. And is there temptation since
• 16:15
  you kind of have a, a tech enabled service to raise around
• 16:19
  or I mean, I'm a I'm a bootstrap guy.
• 16:21
  I love that, you know, but you're, you're sitting in that
• 16:24
  way. You, you, there's big pockets
• 16:26
  floating around looking for opportunities.
• 16:28
  How do you kind of approach the the idea?
• 16:32
  So we, we just started talking to investors and I, I think
• 16:37
  there's some, there's some investors that we are driving
• 16:41
  with in the sense that our vision is.
• 16:44
  And I can't even, I can't even own this term because this,
• 16:48
  this, this term was given to me by a office investor named Kevin
• 16:52
  Mcaffery called service as a software.
• 16:55
  So the model of software as a service or SAS is being flipped
• 17:00
  where companies are now for the first time ever able to provide
• 17:04
  a service, which is what we do, and automate that on the back
• 17:07
  end with software, which gives a service software like margins.
• 17:13
  And to someone like Kevin, that's a very appealing
• 17:16
  proposition. I think what we're seeing is for
• 17:19
  more mainstream investors, they're still coming around to
• 17:24
  this concept and whether or not it's possible.
• 17:27
  It's an amazing thesis to believe that you could take some
• 17:30
  of these service businesses and give them software margins, but
• 17:33
  you actually have to prove that. And so the, I think there is
• 17:36
  some investors we're meeting with that share that thesis of
• 17:39
  service as a software and that AI has unlocked that automation.
• 17:44
  And with the right expert team in a very specific domain, this
• 17:48
  is possible. But they're still investors that
• 17:52
  are not yet on board with that thesis or don't believe it's
• 17:56
  possible to play out yet, and that we still need more
• 17:59
  innovation on the AI technology to be able to get there without
• 18:05
  human human involvement 1. Percent, you know, and I think
• 18:09
  that's a it's a great medium point.
• 18:11
  I think it was Peter Thiel that said talked about, you know,
• 18:14
  service as a software, you know, because there's a lot of
• 18:18
  apprehension about AI, particularly with people that
• 18:21
  aren't kind of like on the leading edge of this stuff, A
• 18:24
  lot of enthusiasm, obviously, but you know, I, I'm in my own
• 18:27
  little bubble, you know, where other people are like, I don't
• 18:30
  want, you know, I don't like to use my debit card.
• 18:32
  I write checks. There's people in varying
• 18:34
  states, stages of tech adoption, you know, but but services and
• 18:39
  software like basically keeps the human in the loop, which I
• 18:42
  think is going to be a very important component for a very
• 18:45
  long time. How efficient is that person in
• 18:49
  the loop and what decisions are they making?
• 18:51
  Comes down to like the the quality of the service.
• 18:54
  I think you know, where it's like, Hey, we can we have this
• 18:56
  automated. This is where I'm, you know, Q
• 19:00
  seeing it in some capacity or adding a little something.
• 19:03
  You know, when I was kind of doing research on you, one that
• 19:07
  was a great quote that stood out.
• 19:08
  You know, it said AI is a tool, the ideas inside experience that
• 19:12
  still comes from me. How how soon do you think you'll
• 19:16
  start to let AI have the insight and experience or ideas?
• 19:23
  Yes. I, I agree with you in the sense
• 19:26
  that I, I still feel strongly that today we're at a place
• 19:30
  where human in the loop is more powerful, especially as a
• 19:34
  marketer. The power and marketer is the
• 19:37
  human insight You are selling to humans.
• 19:40
  Marketing is a very human craft. The pieces that, so the way that
• 19:46
  we see it splitting is that there's like any job function,
• 19:52
  there's a lot of manual work that's repetitive and those are
• 19:56
  the pieces. So you see this in finance.
• 19:58
  Finance is a lot, there's a lot of pieces on the analysis side
• 20:01
  that are very repetitive. But at the end of the day,
• 20:04
  you're doing that analysis, analysis to to present insight
• 20:09
  that's going to drive your business.
• 20:10
  And often that insight is very human.
• 20:13
  The same thing is the case in marketing.
• 20:16
  So our the way that we see it with our business is that.
• 20:21
  Our our end customers, which are businesses that are that are
• 20:25
  looking to drive more organic inbound, they're looking to
• 20:28
  drive more customers at a lower price than advertising.
• 20:32
  What they want in a service provider is they don't want to
• 20:36
  think about all that manual work.
• 20:38
  They want you to do it. So our job is to figure out how
• 20:40
  do we do that faster so we can provide better service to them.
• 20:44
  But what they want from us is also a human that understands
• 20:47
  them and their business. And so I still think we are a
• 20:50
  ways from that human interaction or that human expert that
• 20:54
  they're working with. So for us, we look at it as the
• 20:57
  service part. A lot of that is actually the
• 20:59
  human interaction. You have the, the monthly or
• 21:02
  biweekly phone call you have with an SEO or AI search expert
• 21:07
  that's helping understand your business and then put that into
• 21:11
  a project plan that then their software is helping them to
• 21:14
  automate and execute faster. And I think the same, it's the
• 21:18
  same what when I look across marketing, there's definitely a
• 21:24
  lot of it that could be automated, but that fundamental
• 21:27
  human insight, AI is not there today because marketing is a
• 21:31
  route differentiation. And so you need to have a lot of
• 21:35
  context to do something different.
• 21:37
  And AI is not great. AI is great about context.
• 21:41
  It's not great about doing something different.
• 21:44
  I love that, you know, I, it is great for, I like to use it as
• 21:48
  kind of like a rough draft with ideas.
• 21:50
  I was really hesitant to like give it my ideas muscle because
• 21:55
  it's something I value about myself, you know, but you can be
• 21:58
  like, hey, give me 21 ideas about XYZ and then you now
• 22:01
  you're an editor and you're like, OK, no, actually those two
• 22:04
  I really like. And then you can start to expand
• 22:06
  upon it. You know, I kind of equate it to
• 22:09
  like being a sculptor as opposed to a painter.
• 22:11
  With a painter, you're trying to put your ideas on and then with
• 22:14
  a sculpting, you're trying to take everything off of your
• 22:17
  idea, you know, so it, it could be interesting there.
• 22:20
  Now I want to take a quick break here and let everybody know that
• 22:23
  Jenna has agreed to break down step by step how companies can
• 22:28
  utilize LLMSEO for their own companies.
• 22:32
  And like what's going to differentiate between doing
• 22:35
  specific tasks for the LL Ms. We're going to put that on
• 22:38
  YouTube. So go to YouTube right now and
• 22:40
  watch that short video if you want to know how you implement
• 22:44
  some of these ideas. Now, Jenna, when I look at you,
• 22:48
  there's something I see that I really like and that is right
• 22:52
  behind your right shoulder is a big square that says deals.
• 22:56
  And being a being an an agency work and service provider for
• 23:00
  many, many years, you realize that really it comes down to
• 23:03
  being a sales organization. So when you think about creating
• 23:08
  repeatable sales processes for your service agency, how do you
• 23:11
  guys go about it? Oh, this is the $1,000,000
• 23:16
  question. This is the hardest part of our
• 23:18
  industry because SEO is super, highly fragmented.
• 23:22
  There's a ton of service providers, there's freelancers,
• 23:24
  there's agencies. You as a business have a ton of
• 23:28
  options. So it's very hard to stand out
• 23:32
  because you have a lot of competition.
• 23:35
  For us, I don't think we differentiate in the tactics to
• 23:39
  to get to the customer. The big differentiation for us
• 23:43
  is in the product and service that we provide, which is it's
• 23:47
  not an SEO black box. You can see exactly what we're
• 23:51
  doing. We give you full visibility and
• 23:53
  we give you the controls. So if you want to log into your
• 23:56
  dashboard and you want the dials to run your own organic
• 24:00
  marketing, we provide you those. We are also just providing you
• 24:04
  with an expert, so a service on top.
• 24:07
  So to us, we don't think we, we think we're fundamentally a
• 24:11
  different beast than the agencies that you might be
• 24:15
  considering US against. But the in terms of tactics,
• 24:20
  well, it's all, it's all the same stuff.
• 24:26
  How to reach businesses SEO. Exactly.
• 24:29
  The funny thing about SEO is it's hard to rank.
• 24:31
  It's the hardest thing to rank for because everyone in the
• 24:34
  space is an SEO expert. So you're competing against the
• 24:38
  best. But a lot of most of our
• 24:41
  businesses today actually comes through LinkedIn.
• 24:44
  So most of them have come through me writing content on
• 24:47
  LinkedIn. And the way that I do content on
• 24:49
  LinkedIn is, is quite simple. Every week I sit down and say,
• 24:53
  what did I learn this week either about our customers or
• 24:57
  the industry? What can I share that will
• 24:59
  provide value to businesses? And that's what I do every
• 25:02
  single week. If I write, here's what I
• 25:04
  learned. And if those insights are
• 25:05
  helpful to folks, they reach out to us.
• 25:07
  Amazing. It's so cool.
• 25:11
  So LinkedIn as a as a, a driver, it Linkedin's is very hot or
• 25:15
  cold for me as well. Like sometimes it'll you just
• 25:18
  have a thread where it just, it works and clicks and other times
• 25:22
  not so much. Do you find?
• 25:24
  And I seem to be throttled right at about 1200 views per week,
• 25:28
  what with whatever I do. Do you notice kind of similar
• 25:30
  patterns with LinkedIn as a marketing channel?
• 25:34
  I think it's like any marketing channel you it's a bit of a
• 25:38
  slog. Yeah.
• 25:40
  So I think the. Most common thing is that I was
• 25:43
  AI was a fractional CMO before I started hotter.
• 25:46
  And I think the biggest problem I saw can be into companies was
• 25:50
  doing too much. We're trying to do all the
• 25:52
  channels and by the nature of that we're doing none of the
• 25:54
  channels well. But as a business, you really
• 25:57
  only need one or two marketing channels to work to be a very
• 26:01
  large business. You go into businesses I was at,
• 26:04
  I was at Uber previously. You go to a business like Uber,
• 26:06
  we've usually had about two main marketing channels that were
• 26:10
  driving most of our acquisition. And so the, a lot of marketing
• 26:16
  is figuring out how to unlock a channel, which takes time.
• 26:20
  And I feel like LinkedIn has been that for me.
• 26:23
  I had AI had a very hot start with LinkedIn.
• 26:25
  So I, I told my story about my time at Uber on LinkedIn and the
• 26:31
  views on that. I, it was huge.
• 26:33
  It was like 150,000 views on my second post on LinkedIn.
• 26:39
  So I'm like, oh, this platform's amazing.
• 26:41
  And then after that, after that, the, all the posts bombed.
• 26:46
  And then I realized it's just, you just have to keep going.
• 26:50
  And so I tried to be very consistent.
• 26:52
  I tried to write articles every two weeks and some will go.
• 26:57
  I noticed LinkedIn is a very slow burn.
• 27:00
  So unlike other platforms where if the post like X is very much,
• 27:04
  the post has to succeed in the first hour for it to continue to
• 27:08
  be shown. Instagram is very similar.
• 27:11
  LinkedIn has a much slower burn. I will see articles that I've
• 27:14
  written five days later start to catch momentum.
• 27:19
  So I, I don't feel like I've dialed in what works first, what
• 27:25
  doesn't other than the high level or call it generic
• 27:29
  learning, which is the more value can you can provide for
• 27:33
  folks on there, the more engaged they're going to be with your
• 27:37
  content. And so I keep going back to what
• 27:40
  did I learn this week that's going to provide value to
• 27:44
  someone else that's trying to build a business?
• 27:46
  Nice. I'm going to give that a shot.
• 27:48
  Although the biggest thing I've ever had to go virals about Home
• 27:52
  Depot hot dogs. You know what I mean?
• 27:53
  It's like you don't know what you're doing out here.
• 27:56
  True I. Haven't tried that strategy.
• 27:58
  So some folks will do the memes and get a lot of engagement with
• 28:01
  that. I haven't tried that strategy.
• 28:03
  I've heard it's also hit or miss.
• 28:04
  You know, some some games hit. That's the nature of a meme,
• 28:08
  yeah. Most do not.
• 28:10
  Cool, Jenna, you keep giving us these little hints.
• 28:12
  You know, you, you live in Calgary, you're in LA now, you
• 28:15
  worked at Uber, you bootstrap to start up.
• 28:18
  Like how did all this come about?
• 28:20
  How do you find yourself sitting in the seat you are today?
• 28:23
  Also on your left shoulder it says feel good.
• 28:25
  I also really appreciate that too.
• 28:29
  Yeah, I feel it's funny. I thought about erasing this
• 28:32
  before starting and I was like, you know what, We might as well
• 28:34
  just show how the sausage trees made.
• 28:37
  So my, you know, my story, my story's a bit unique.
• 28:43
  So I, so I grew born and raised in, in Calgary, didn't know much
• 28:47
  about technology, didn't know anything about Silicon Valley,
• 28:52
  went to school in LA at USC and started my career in the
• 28:54
  entertainment industry. Quickly found entertainment was
• 28:58
  not my tribe and I I got into the hobby of kite surfing.
• 29:04
  What did you wait? What did you do in
• 29:05
  entertainment? I worked on a talent agency.
• 29:10
  So I worked at a talent agency called Prince Potter Young and I
• 29:13
  did internships, music business prior.
• 29:16
  So I was at a universal was my college internship in the
• 29:20
  licensing department. And so I, I figured I wanted to
• 29:24
  build a career in Hollywood and entertainment and I, I didn't
• 29:28
  love the structure of that business.
• 29:30
  I didn't find it the most intellectually stimulating.
• 29:34
  And my hobby after college was kind of surfing.
• 29:36
  And through kite surfing, I met a venture capitalist.
• 29:40
  This is actually the VC who was the first investor in Canada.
• 29:43
  So comes full circle. An investor named Bill Thai met
• 29:48
  him kite surfing and he introduced me to basically tech
• 29:52
  and entrepreneurship. And I was just fascinated.
• 29:56
  It just, it blew my mind that people just came up with an idea
• 30:01
  and built the company. And I actually met Mel, the
• 30:04
  founder of Canva, during that journey on a kite surfing trip.
• 30:08
  And she was very young and had this vision for Canva.
• 30:11
  And I thought it was so cool. People were just building stuff,
• 30:14
  just coming up with stuff and building stuff.
• 30:16
  And so when I was 22 and I was working in entertainment and I'd
• 30:22
  met Bill and I'd called Bill and I and I asked him if I could
• 30:26
  come to San Francisco and shouting, you know, you're 22,
• 30:29
  you don't know any better. You assume that's a reasonable
• 30:31
  question. And Bill was like, sure.
• 30:34
  So I drove up to San Francisco and I went to pitch meetings
• 30:37
  with him and in between the pitch meetings he would explain
• 30:41
  to me how these businesses work, why this was interesting, why
• 30:44
  this wasn't interesting, and I just fell in love with Silicon
• 30:48
  Valley and tech. And so through, through that
• 30:51
  journey, I found the first start up that I went to work for and
• 30:55
  ended up working at several start-ups since found my way to,
• 30:59
  to Uber in 2016 and actually was hired to work on Uber Eats when
• 31:05
  it was a, a test product within Uber.
• 31:08
  So Uber had, it was kind of a fun structure under Travis,
• 31:11
  where Travis would essentially allow anyone to explore an idea.
• 31:16
  If you could get enough people internally on board to run some
• 31:19
  tests for a new idea, he would let it run so he wouldn't shut
• 31:23
  things down. So people internally were coming
• 31:25
  up with all sorts of things. And when I was hired, I was
• 31:28
  hired to work across all of these strike tests that were
• 31:33
  happening that the company was like, we, we don't want to put
• 31:37
  too much resources into these, but try to help some of these
• 31:41
  internal entrepreneurs figure out how to go to market with
• 31:45
  these businesses. Ubereats was just one of the
• 31:47
  ones that I was staffed on. And then of course, you know the
• 31:50
  story today that that business ended up becoming successful
• 31:55
  when I, when I started on it, it was actually a different
• 31:57
  concept. The concept was we have all
• 32:00
  these cars on the road as that as Ubers that are transporting
• 32:06
  riders and we have a slow down during lunch when everyone is
• 32:10
  eating. But these cars are on the road
• 32:12
  with access capacity. They have empty trucks.
• 32:16
  So the initial idea was let's fill the trunks with sandwiches
• 32:19
  and burritos and let people order in a 2 hour window that
• 32:24
  particular item for lunch for the day.
• 32:27
  And that worked OK. People were ordering.
• 32:30
  They had a very specific radius, but we weren't selling out
• 32:33
  everyday. But those customers kept writing
• 32:36
  into us and saying, hey, can can we choose a restaurant?
• 32:40
  Is it possible to order from a particular restaurant?
• 32:43
  And so another actually a team in Toronto said, OK, we'll take
• 32:47
  that and we'll run with it. And they started building a
• 32:51
  version of this experiment where folks can order from a
• 32:54
  restaurant, and that's now Uber Eats as it is today.
• 32:58
  Once that started working, essentially we are launching a
• 33:00
  new city every single week. And we did that for about 70
• 33:04
  weeks. It was wild.
• 33:06
  Amazing. So that's, that's kind of my
• 33:08
  story, but I've always been a marketer.
• 33:11
  So getting to SEO and getting to marketing automation seemed like
• 33:16
  a a logical next step after my journey at Uber.
• 33:22
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• 33:30
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• 34:16
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  think bolder with AI for Founders.
• 34:22
  Now back to the show, it was rumors back in the day that Uber
• 34:26
  was this weird boys club when they're acting foul.
• 34:28
  You have any experience with that or was it pretty chill?
• 34:32
  It was not chill. It was not chill.
• 34:37
  Actually, that's part of the way I went there.
• 34:40
  I so I have, I have two older brothers.
• 34:42
  So, so I always grew up like trying to keep up with, with two
• 34:47
  older brothers that are very close in age.
• 34:49
  And I remember I was working at a start up and I was like, this
• 34:51
  is too chill. I want to go to a place where
• 34:55
  people are really motivated and really passionate about the
• 34:58
  mission. And I remember explaining to
• 35:00
  friends at the time that I think I'm going to go to Uber and
• 35:02
  you're like, you're crazy. Everyone talks about how working
• 35:05
  there is so difficult and that the culture is terrible.
• 35:08
  And I got in there and I loved it.
• 35:10
  I was like, wow, people here are like hard charging and rude and
• 35:15
  everyone, but in a good way. People care deeply about this
• 35:19
  mission because once you got in there, you were like, this
• 35:21
  product's amazing. Like the freedom it gives people
• 35:24
  is game changer. I remember the first time I
• 35:26
  tried the product, I was like, wow, I can travel around San
• 35:29
  Francisco. I don't have to go home before
• 35:30
  midnight to get on the Bart so I don't miss the last train.
• 35:33
  I literally press a button and someone takes me home and I'm
• 35:37
  safe. This is wild.
• 35:39
  So I think that the internal matched the external perception
• 35:43
  in the sense that it was a very hard charging culture.
• 35:46
  The expectations were very high and the speed was incredible.
• 35:51
  Just just the expectation of how fast you need to go to keep up
• 35:56
  was wild. So very long hours.
• 35:59
  The bad stuff definitely what? Any company that hires 6000
• 36:04
  employees is in a year is going to have an HR problem.
• 36:07
  Yeah. That was expected.
• 36:10
  It could have been handled better.
• 36:13
  There's definitely some missteps throughout the journey, some
• 36:17
  leadership missteps, but I still fundamentally believe that it's
• 36:21
  a great company. Yeah, why'd you leave?
• 36:27
  And it just changed. So I was there through the IPO
• 36:32
  and we went from being what felt like a start up journey to a, a
• 36:38
  public company. That's when the the trained
• 36:41
  executives came in. We had to put a lot more
• 36:44
  structure and process in place. So it just felt like a different
• 36:47
  company. I had been there for four years
• 36:50
  and it was four years of massive growth.
• 36:54
  And so, you know, you start to get tired of the long hours and
• 36:59
  also you've gone through so much chase like we had so many
• 37:02
  reorgs. You're heading reorged every two
• 37:04
  months. Projects were changing, new
• 37:07
  leadership was coming in. So I just felt like it was time
• 37:10
  to to, to try something new. I unfortunately left in 2020,
• 37:17
  February 2020, and I bought a one way ticket to Asia.
• 37:23
  Yeah, I bought a one way ticket to Asia.
• 37:25
  And in February, I was like, I'm just going to go travel Asia and
• 37:28
  I'm going to think about what I want to do next.
• 37:30
  And I was. There for every month exactly.
• 37:33
  I was in Asia and it was empty. It was spooky.
• 37:36
  I was on a plane. I took AI took a flight from
• 37:39
  Bali to Singapore and I was on a full, full 747 two people.
• 37:46
  And that's where I was like, all right, I think I think it's time
• 37:49
  to get out of here. And I returned.
• 37:50
  I think it was like 3 days before borders closed.
• 37:54
  Wow. And then that, that was time to
• 37:57
  figure out, OK, what's next year?
• 37:59
  Yeah, what a story. Amazing.
• 38:01
  Are you ready for the Lightning Round?
• 38:05
  Yes, yeah, we'll do it here. We.
• 38:07
  Go. Let's say you sell Hatter
• 38:09
  tomorrow for a billion dollars. What's your next project?
• 38:15
  Oh that's a tough one. My SO, my Co founder and I are
• 38:22
  actually very passionate about finance automation and we have
• 38:25
  this belief that a lot of what's happening, the manual work in
• 38:29
  financial analysis could be automated and treated like
• 38:32
  analytics and if we weren't building Hatter we would be
• 38:35
  building that. Love it.
• 38:38
  If you were to to start a company tomorrow that would net
• 38:42
  you $1,000,000 at the end of the year, what what would that
• 38:45
  company do? World's funny and the start of
• 38:56
  journey and figuring out where we wanted to focus.
• 38:58
  We found millions of these nice things where we're like, if we
• 39:01
  just did that, trying to think of what some of those were, They
• 39:06
  were, they were simple things like e-commerce tax tools, very
• 39:11
  getting, very neat. But I don't think I could give
• 39:14
  you 1 of like if I just wanted to make $1,000,000, what would I
• 39:16
  do? Because maybe I might be doing
• 39:17
  that. Yeah, I like it.
• 39:20
  I like it. If you were entering college
• 39:24
  today and you weren't studying entertainment business, what
• 39:26
  would you study based on what you know now?
• 39:31
  Oh, pants down, computer science.
• 39:33
  Computer science still. Yeah, So I, so I, when I went to
• 39:37
  college, I, I started in journalism and I, they, the
• 39:42
  computer science school didn't have enough students.
• 39:45
  And they presented to our journalism class about computer
• 39:48
  science and they gave us a pamphlet with a, with a puzzle
• 39:51
  that you could go home and do and see if you were interested.
• 39:54
  And I went home and did this puzzle where you had to code
• 39:56
  this robot through a maze. And I was like, oh, this is
• 39:58
  super cool. Maybe I should actually look at
• 40:00
  this and take some courses. And I called my dad, my dad's a
• 40:03
  geologist and he does a whale exploration and he's like, oh,
• 40:08
  sweetie. The, the computer scientists,
• 40:10
  they don't make very much money. These are.
• 40:12
  These are like the people who sit in the basement and they
• 40:14
  code and they're kind of at the bottom of the totem pole in the
• 40:20
  oil industry. I don't think he would be happy
• 40:23
  doing that. So decided not to and then two
• 40:27
  years after college ended up in tech and it was like that would
• 40:30
  have been a great being technical in in space would have
• 40:34
  been a great skill to have. And even now I'm fascinated
• 40:37
  talking, fascinated talking to my Co founders get Co founder
• 40:41
  getting into the details of building Yeah.
• 40:44
  So if I. Could do it over again, yeah.
• 40:46
  Now, senior engineers were just getting like, you know, like
• 40:50
  draft picks for professional athletes with $10 million annual
• 40:55
  contracts. Incredible.
• 40:57
  That's true. Those are that $100 million
• 40:59
  fanning bonus for the AIDHDS. Looks nice.
• 41:04
  It does look real nice. OK, last one here and probably
• 41:08
  the hardest one. With everything you know now,
• 41:11
  what's something that you wish you knew earlier?
• 41:19
  Oh man, so much. I'll, I'll, I'll, I'll give one
• 41:22
  that I think is useful for founders.
• 41:27
  I think that we've learned that the journey to product market
• 41:31
  fit is very different than we expected.
• 41:35
  Kind of the conventional wisdom is you have this idea and it's
• 41:39
  all about the idea and then you go and get funding for that and
• 41:43
  then you figure out how to make this idea kept alike.
• 41:46
  It's not like that finding product market fit is actually
• 41:51
  finding a problem that you are obsessed with.
• 41:56
  Find a problem that you care about solving and understand
• 42:00
  deeply how that problem works for that customer and don't
• 42:03
  build anything until you've spoken to 100 customers.
• 42:07
  And so the way that we approach how to validate an idea is so
• 42:13
  different. We no longer start with an idea
• 42:15
  and then say, let's go figure out how to make that come to
• 42:18
  life. We start with a problem and we
• 42:22
  just search for problems and there's problems everywhere.
• 42:24
  I remember years ago I was in a car with one of the founders of
• 42:29
  Uber, Garrett Camp, and he's just, he's obsessed with this.
• 42:34
  He travels around with a little notebook and he just looks for
• 42:39
  problems and we're in the car and he's like, what do you guys
• 42:42
  think of air conditioning? We're like, oh, it's not great.
• 42:46
  You're always fiddling with it. It's like too strong
• 42:48
  temperatures, never fully right. He was like, what would make air
• 42:51
  conditioning better? People in the car are like, oh,
• 42:54
  what? It's weird that air conditioning
• 42:55
  doesn't detect the temperature outside.
• 42:58
  And they said, can someone look up the air conditioning market?
• 43:00
  How big is the air conditioning market?
• 43:02
  And then someone searches and was like, this is how big it is.
• 43:04
  And he's just taking notes and he's like cool. 10 minutes
• 43:08
  later, something similar. What do you guys think about
• 43:10
  this? Is this a problem?
• 43:12
  Takes notes. And so I think I wish I knew
• 43:17
  that earlier. There's so much lower in Silicon
• 43:20
  Valley and startup culture around like you have to have an
• 43:22
  idea to start a company. You don't.
• 43:24
  You just need to be good at finding problems and talking to
• 43:27
  people and listen. That is the biggest piece is
• 43:31
  understanding why someone needs to solve that problem
• 43:33
  fundamentally before you ever build anything.
• 43:38
  Rochelle, Jenna Han And this has been extraordinary.
• 43:41
  I'm assuming LinkedIn is the best place to connect with you.
• 43:46
  Yes, OK, I'm on there regularly. Cool.
• 43:49
  We will link that in the show notes here.
• 43:50
  Thank you so much for coming on the show.
• 43:53
  Thanks Ryan. I appreciate the time.
• 43:57
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  audiences, and optimize every metric that matters.
• 44:54
  At Moeburst, we believe that creative thinking, advanced
• 44:57
  technology, and data are the core drivers of success at
• 45:00
  scale. If you're serious about scaling
• 45:02
  your business with precision and purpose, it's time to talk to
• 45:06
  Moeburst. Visit moeburst.com and let's
• 45:09
  build something category defining together.