What VCs Actually Want Beyond an AI Demo | Rebecca Lynn, Canvas Ventures

Name: What VCs Actually Want Beyond an AI Demo | Rebecca Lynn, Canvas Ventures
Duration: 10 min 48 s
Description: Rebecca Lynn is Co-Founder and Managing Partner of Canvas Ventures, an early-stage venture capital firm focused on fintech, digital health, and AI investments.

EO10:48Added Aug 31, 2026

Rebecca Lynn is Co-Founder and Managing Partner of Canvas Ventures, an early-stage venture capital firm focused on fintech, digital health, and AI investments. Having led the investment in Lending Club's $1B IPO during her previous role, and now steering Canvas Ventures to successes like Casetext's recent $650M exit to Thomson Reuters, she brings deep expertise in spotting transformative startups. In this interview, Rebecca shares five essential

Watch on YouTube →

Contributed by 刘嘉琪

Transcript

00:00is it's really easy to create a company
00:02in gen in demo mode it is a very
00:06different thing to take that beautiful
00:08demo and put it in the wild and scale it
00:10and we've already seen a handful of
00:12companies that you know were backed by
00:14amazing investors kind of blow up
00:16because they weren't able to transition
00:18from that really cool slick demo into
00:20the wild essentially into full
00:21production the biggest question we have
00:23for companies is they come to us and we
00:25like the beautiful demo come to us when
00:27you have a customer that's live
00:33my name is Rebecca Lynn I'm the founder
00:36and managing partner of canas Ventures
00:38canvas Ventures is an early stage
00:40Venture Capital firm that focuses on
00:43investing in financial services digital
00:45Health Andi so some of the most recent
00:47outcomes of canvas Ventures are case
00:50Tech Gabby and futur advisor and
00:53importantly case text was a very early
00:56exit with AI and gp4 and they exited to
00:59Thomson reuter about 650 million Gabby
01:02was acquired by Experian and future
01:04adviser by Black
01:08Rock so I have always been a believer in
01:11in second mover I think first mover
01:13Advantage is a fallacy and the reason is
01:15is that it takes a lot of money and time
01:18and patience to really prove out a brand
01:21new market and once you prove it out you
01:23have a ton of technical debt I invested
01:25in Lending Club and from then on Lending
01:28Club ended up being the largest US tech
01:30IPO in 2014 and so lendy Club wasn't the
01:33first mover there was a company out
01:34there called Prosper who had really hit
01:36the market first the best position to be
01:39in in my opinion of a company is the
01:41startup that lets another company kind
01:43of seed the market prove that there's a
01:45market there and then they can take that
01:47learning and come up very quickly with a
01:49better product and better marketing and
01:51no technical debt I would challenge
01:53anyone to to come up with more than just
01:55a handful of companies that are public
01:57today that truly were the first mover
02:00there are very
02:03few I think the most important
02:06characteristic of a CEO is salesmanship
02:08really a CEO's job all the time is sales
02:10you're selling to your customer you're
02:12selling to your employees you're hiring
02:14people you are constantly selling the
02:16company that in my opinion really most
02:19clearly defines a CO who listens to
02:21their customer and then is a great sales
02:24leader it was Jeff tagney at doximity he
02:27from the very beginning brought on a
02:30customer advisory committee to help
02:32inform him of you know what was
02:34important to his end users in the
02:35product and what wasn't and where to
02:37take it very early on he would bring in
02:39this advisory panel to like an on-site
02:42sort of strategy session and they would
02:44wireframe me of five six seven different
02:46ideas and show them to this you know
02:49panel of end users that would really
02:51feed into their entire product road map
02:54and he did that from the beginning so
02:55when I'm evaluating whether a CEO really
02:58possesses sort of the salesman ship it
03:00becomes blazingly obvious as they're
03:01pitching us you want a CEO who can sell
03:05you on their Vision because of their
03:06excitement and how they thought about it
03:08and that they've talked to the consumer
03:09and you also want them to be incredibly
03:12honest and forthright with you as the
03:14same time because that's what ERS trust
03:16when you're in the sales process so when
03:18we ask a CEO about you know their ARR
03:21and is it booked or is it forecasted
03:23having that c be very open and
03:26transparent and upfront I think shows us
03:28that they are going to not only earn our
03:31trust but the trust of their customers
03:32and that's really important especially
03:34early
03:37on the mistake most startups make when
03:40they're scaling is that they believe too
03:43early they have product Market fit and
03:45they believe they they've got it and
03:46then they go out and they hire a very
03:48expensive salesperson who then wants to
03:50hire a bunch of people and they just
03:52burn a ton of cash too early and then
03:54they have to let that salesperson go and
03:57then go back to the drawing board and
03:59kind of sort out a little bit more you
04:01know what those elements of product
04:02Market fit are and then rehire it's hard
04:05to watch I think almost every startup
04:07does this especially in the Enterprise
04:08space and and our advice is you know
04:10just way to beat hire maybe that
04:12director level salesperson who can help
04:15you maybe a chief of staff that can help
04:17you in in your sales efforts and then
04:19really make sure you scale gradually
04:22when you think you have product Market
04:24fit have some more checkpoints you know
04:26before you go out and pay a lot of money
04:28for a head sales person person before
04:30you have product Market fit you know
04:31what there's an example so case text
04:33pretty early thought they had product
04:35Market fit and they hired a very good
04:39you know Season sales executive to come
04:41in they spent quite a bit of money on
04:43the sales exact and the team and it it
04:45wasn't working they weren't getting the
04:47traction that they had hoped for this is
04:49before they launched co- counil the GPT
04:524 product the founder to his credit made
04:54a pretty quick early decision to let
04:56that team go and it was really hard you
04:58know the salesperson was great it wasn't
05:01an issue with them it was an issue with
05:03you know where we were at that time with
05:04the product you know it was really about
05:06supporting the founder he kind of saw
05:08also that was the right answer but it
05:10was a hard answer it was a hard thing
05:11for him to execute and so helping him
05:14think through how to message it how to
05:16make that happen and introducing him to
05:18other Founders who've had to make
05:20similar tough choices so that he can get
05:22their firsthand experience and advice
05:24was really helpful often times the
05:26founder does have Instinct and data that
05:29I don't so I first seek to understand
05:31why they're heading in the direction
05:33they're heading and then if we become
05:35pretty convinced that it is the wrong
05:37direction we try to show not tell and so
05:40we we try to find the right people to
05:42introduce them to that will offer them
05:45you know a more complete picture of the
05:47way we're thinking about the world and
05:48often times we get there it's not that
05:50they were completely in the wrong
05:51direction and we were right often times
05:52there's some kind of meeting in the
05:53middle I think the first thing that we
05:55need to do is check our assumptions
05:57understand where the founder is coming
05:58from and then get them the resources if
06:00they do need to make a shift and they
06:02decide they make a shift like help them
06:04on that journey and it does happen I me
06:06there's I think every company it's often
06:07times many stages you has to Pivot
06:09either from strategy or product or
06:11Channel or you know whatever it might be
06:13and when they they get there you know
06:14our job is to help them figure out how
06:17to make that
06:20shift what do you do when a potential
06:23client says we love your product but
06:25it's way too expensive do you give in on
06:28discounts right away or can you
06:30confidently defend your price hi I'm
06:33Peter on with over 15 years of sales
06:36experience at companies like Google
06:39Dropbox and slack I've obsessed over how
06:42to effectively answer questions like
06:45this in a way that builds trust that's
06:48why I created Peter on sales school with
06:51EO to equip startup Founders and sales
06:54professionals with the modern skills to
06:56excel in Enterprise B2B sales this
07:00online course offers real life examples
07:03and ready to use B2B sales Frameworks
07:06that you can incorporate immediately
07:09from crafting the most effective pitch
07:11deck to authentic customer Discovery and
07:14even negotiation I walk through how you
07:16could do it all and limited to just 10
07:19students I'm also offering oneon-one
07:22bespoke feedback on assignments ready to
07:26learn and grow your sales confidence
07:28check out the link in the description or
07:31find me at EO
07:33[Music]
07:35school so there's a ton of opportunity
07:38in gen the clear thing that we has come
07:41to us is it's really easy to create a
07:44company in gen in demo mode to create
07:46this beautiful demo that blows everyone
07:49away it is a very different thing to
07:51take that beautiful demo and put it in
07:53the wild and scale it and we've already
07:55seen a handful of companies that you
07:57know were backed by amazing invest ERS
07:59kind of blow up because they weren't
08:01able to transition from that really cool
08:03slick demo into the wild essentially
08:05into full production the biggest
08:07question we have for companies is they
08:09come to us that's a beautiful demo come
08:11to us when you have a customer that's
08:12live for the CEOs who come to us to
08:14pitch sort of their series A and B
08:16companies and even we look at a lot of
08:18seed deals also the questions I ask are
08:21really about how's the consumer using
08:23the product what have they learned from
08:25the consumer since they started the
08:26company what was surprising to them what
08:28thesis proved what was different and
08:30what I'm looking for is that they're
08:32listening they're actually looking for
08:34that feedback from their users and that
08:36they're listening and they're adjusting
08:38accordingly right that they're not sort
08:39of dogmatically adherent to maybe
08:42solving their own problem that was what
08:44you know the company stem from that
08:46they're listening to what their end
08:47users really want and need the second
08:49thing I really look for from the CEOs is
08:51what gets them out of bed in the morning
08:53they really motivates them to do a
08:55startup because there's going to be
08:56really really hard times in the startup
08:58there always are what is it about them
09:02that is driving them forward what's
09:03going to help them pick themselves up
09:04when things get really hard and Shake
09:06themselves off and keep going and so I
09:08always like to hear the CEO's stories
09:10all of them could easily go get a job
09:12and get paid you know quite a bit of
09:13money at a big company and what is it
09:15about this particular opportunity that
09:17is really energizing
09:21them I was motivated to found cus
09:24Ventures because I wanted to create the
09:26Venture firm that I would want to fund
09:28my startup I didn't start inventure
09:31Capital thinking I would be here you
09:32know a decade plus later when I started
09:34in Venture Capital it was really a GU I
09:37was going to start Venture Capital learn
09:39how they made decisions and I was going
09:40to get them to invest in the company
09:42that I was working on and unfortunately
09:44I enjoyed the job so much that I I
09:46remained adventure with canvas this is
09:49my startup and one of the things I I try
09:51to stress is just be more confident in
09:53yourself one of the most formative
09:55things was you know what my best friend
09:56from business school where we're taking
09:58a leadership class
09:59and we had to rank ourselves we had all
10:02of these things and we had to rank you
10:03know one through five you one being the
10:05best how good you were at everything and
10:07then we had to get up and say what we
10:09ranked ourselves and you know everyone
10:10was pretty you know I don't know modest
10:13or whatever and she's like I'm a one I
10:15was I was like who is this person right
10:17and she just explained in the world of
10:19banking that's the first thing they
10:20teach you like fight for yourself
10:22because you know you're working for
10:23somebody else and why would anyone want
10:25to hire you unless at least you believe
10:27that you were the best possible person
10:29for that job and that really stuck with
10:31me you know why would I expect somebody
10:32to invest in me give me money give me
10:34that promotion if I didn't believe I was
10:36the best person for that job be more
10:38confident in yourself no one's going to
10:39believe in you more than you