Financial_Samurai-Emily_Luk_Episode-Final_Version
00:00:00.000 | Hello, everybody. It's Sam from the Financial Samurai Podcast. In this episode, I have a
00:00:12.800 | special guest with me, Emily Luck, co-founder and CEO of Plenty, a wealth platform for modern
00:00:20.680 | couples. Welcome to the show, Emily.
00:00:22.080 | Thanks for having me, Sam.
00:00:24.280 | In this episode, I would love to talk to you about your journey from college to your first
00:00:29.240 | job to working at one of the largest private startups and then leaving. I've been in the
00:00:34.800 | Bay Area since 2001, and I've seen so many people join startups, make it big, but most
00:00:42.640 | don't make it big. Some join the big giants like Google and Facebook and Apple, and they
00:00:47.640 | end up very wealthy over a 10- to 20-year period. I'd love to understand your thought
00:00:52.200 | process and how you decided where to join after college and then your career trajectory
00:00:56.960 | after that.
00:00:57.960 | Yeah, more than happy to chat through it. I think, you know, for me, it really did start
00:01:03.960 | with actually my family upbringing because both my parents and my grandparents, they'd
00:01:09.600 | each built companies for almost 20 years. And so for the longest time, that actually,
00:01:14.080 | to me, was the definition of starting a company. When I was in university, I actually almost
00:01:21.000 | dropped out because I was just ready to start working. Instead, I ended up deciding to graduate
00:01:26.080 | early, but I had a chance to start working in venture capital, which for me, the VC world
00:01:31.680 | was so incredibly important because I was always an ideas person all the way through
00:01:36.480 | growing up. But being in venture and the reason why I decided to start my career in venture,
00:01:41.980 | it gave me an opportunity to have a really analytical framework to understand what ideas
00:01:48.760 | can go the distance, what is something that I could potentially think about, you know,
00:01:53.120 | decades in my life of building and really think about that from the perspective of an
00:01:58.600 | investor. I think one of the things that at the time someone had given me some really
00:02:02.000 | great advice and one quote that really stuck was, "Unlike an investor where you can make
00:02:07.940 | so many different investments, when you're working for a company, you're really making
00:02:11.820 | one bet at a time." And so if anything, it's even more important to think about whether
00:02:17.020 | or not that company is worth betting on.
00:02:19.960 | As a venture capitalist, this is interesting because I think joining the VC industry after
00:02:24.840 | college is one of the most coveted types of industries to join along with investment banking,
00:02:30.680 | management consulting. How did you get the opportunity to join VC? And initially, you
00:02:37.000 | know, how did you gain the confidence to be a VC? Because I've spoken to many VCs and
00:02:42.360 | there are builder VCs, VCs who've started companies so they know the operational, what
00:02:47.080 | it takes and also fundraising and all that. And then there are the MBA graduate case study
00:02:51.960 | VCs who have never built a company. And then, but then many of them still end up being successful
00:02:58.280 | investors.
00:02:59.280 | Yeah. So for me, I've been doing small businesses, running little side hustles all of my life.
00:03:07.960 | Probably the more meaningful business was I started a company when I was in high school.
00:03:12.040 | It was selling customized clothing. It was a way to circumvent the fact that for public
00:03:17.360 | schools you had approved vendors, but student councils could circumvent that. And so I've
00:03:22.520 | been building things like that pretty much all of my teenage years. And so I already
00:03:27.960 | had a track record, I think, of thinking about that framework of ultimately you could buy
00:03:32.760 | something or you produce something and what it costs you to use in order to produce that
00:03:37.920 | good or service is going to be less than whatever you're ultimately selling, hopefully a higher
00:03:41.680 | quality product or service for.
00:03:43.560 | So that framework was something that was fairly deeply ingrained. I was really lucky that
00:03:48.800 | I had that chance to start off in venture. I was 20 years old at the time when I started.
00:03:54.960 | And during that time, actually, how I got that role was because I had worked on starting
00:04:00.400 | companies throughout university as well. And I got involved with a student run venture
00:04:05.200 | fund. This was like back in the days before dorm room fund even existed. And we raised
00:04:10.760 | a small amount of money from a few other corporations with the intention. And we actually did invest
00:04:17.160 | into some student run startups. During that time, we also ran a number of different pitch
00:04:22.800 | competitions for students to actually pitch other VCs. And I was one of the two people
00:04:28.880 | who was leading that at the time. And so when we invited actually some VCs to come to these
00:04:33.600 | pitch nights, I ended up meeting not only the person I end up going to work for, but
00:04:37.840 | actually also the person who is now currently one of our board members for plenty.
00:04:42.720 | Oh, wow. That's fascinating. So it sounds like starting young and getting going and
00:04:48.720 | getting your hands and feet wet is one of the key strategies to getting into VC.
00:04:54.080 | I definitely would say that there's just no substitute for spending time amongst people
00:04:59.000 | who are in, you know, that world. And one thing that I have seen is I have, you know,
00:05:05.280 | talked to many people who have come out of the business schools or the business programs
00:05:08.160 | and asked how to start. And there's actually a much lower barrier to entry than some people
00:05:12.400 | might think, because there's so many of these different events that are happening nowadays
00:05:16.380 | where you just go to the event. There's, you know, tech meetups and all of that where there's
00:05:20.600 | other founders, other VCs. And it's a great environment to be able to learn from, but
00:05:25.960 | then also meet people. And I think one thing that's also been really helpful as a guiding
00:05:30.560 | principle for me my whole career has been that if you're looking to meet someone because
00:05:34.680 | you need someone's help or introduction right now, that's probably like a little late. You
00:05:39.640 | really want to start getting to know people far before you ever even have an inkling of,
00:05:44.480 | oh, maybe I actually might need an introduction from them one day. So it really gives them
00:05:49.000 | time to build a more authentic relationship.
00:05:50.600 | Yeah, it's kind of like if you've been laid off from a firm and you start pinging people
00:05:56.000 | on LinkedIn, it's probably too late. You need to be cultivating those relationships far
00:06:00.400 | in advance with no ask beforehand.
00:06:03.280 | Exactly. I think that's where you build the real relationships where people are willing
00:06:07.120 | to go to bat for you because they don't feel like you're there because you need something
00:06:11.040 | for them right away.
00:06:12.240 | Right. So how long were you doing VC before you moved on to, was it Stripe? What was your
00:06:18.360 | road map after that?
00:06:19.760 | Yeah. So the original plan had been to stay in venture for a couple of years. I would
00:06:24.960 | say I've always had these three to five year plans and never actually followed through
00:06:30.880 | on the entirety of those plans. And life happens and I've kind of moved along with whatever
00:06:36.280 | comes through. And so I stayed in venture for about a year and a half. But right around
00:06:40.960 | that time, I started noticing over the course of my first year in venture that a lot of
00:06:45.600 | companies that were, I was in venture in Canada, and most of the companies we invested in were
00:06:51.040 | Canadian companies expanding into the U.S. market. And one thing I noticed was that most
00:06:55.360 | of our most interesting companies that also, to me, had the savviest technical teams, had
00:07:01.200 | the most interesting businesses or business models, they almost all use Stripe. And so
00:07:06.440 | one thing led to another. I had an individual that I'd known for a long time. He coincidentally
00:07:13.760 | started working at Stripe and I just went to go visit. And I ended up joining them for
00:07:18.480 | a happy hour. He was like, "Yeah, come out to our office. I'll be working there. Let's
00:07:21.720 | catch up." And then one thing led to another. Turns out an individual that I'd sat next
00:07:26.120 | to was actually one of the business recruiters. I didn't think too much of it. We had mostly
00:07:30.480 | just been talking about hobbies and interests. And then a couple weeks later, I got a message
00:07:35.200 | from them about the fact that they were starting to build out their business teams and asking
00:07:40.120 | if it was something that I'd consider moving out to San Francisco for.
00:07:44.320 | What year was that? And at the time, do you recall what Stripe's valuation was?
00:07:49.600 | Yeah. So I moved out to join Stripe in 2015. And at that time, they had just closed that
00:07:56.920 | $5 billion round and they were about a 150, 200 person startup at that time.
00:08:03.680 | Wow. So $5 billion. And so at the time, so you said you noticed the companies you were
00:08:09.560 | investing in were using Stripe more often. What was, I guess, the selling or the value
00:08:15.960 | proposition that made you say, "Okay, I'm going to change jobs and leave my city behind
00:08:21.040 | to come to San Francisco"?
00:08:22.720 | I think one of the things that really jumped out for me for Stripe was at the time, there
00:08:28.480 | weren't really companies that were building great APIs for financial infrastructure. Stripe
00:08:34.240 | was really the first company to come along and do that. And when I actually started looking
00:08:39.880 | through the API documentation to really understand how revolutionary what they did truly was,
00:08:45.800 | if you had gone into a process where you're like, "I built a great product," or, "I
00:08:50.440 | have a company and we're trying to offer this service, and I'm just trying to get paid
00:08:53.840 | for my product or service." If you worked with most of the companies that accepted credit
00:08:58.960 | cards at that time, it was a convoluted process where the product didn't even work very well.
00:09:05.040 | The documentation was terrible. They had all these limitations for what you could do. So
00:09:09.280 | they wouldn't even enable a lot of different business models, especially the marketplaces
00:09:14.120 | or platforms like Shopify or Lyft. And if you tried to get up and running with them
00:09:19.120 | quickly, their answer was, "Oh, let me put you through a sales process. Fill out a sales
00:09:23.600 | form, have multiple sales calls."
00:09:26.160 | And if you think about from the mindset of a lot of people who are builders, they want
00:09:31.680 | to move quickly and they don't necessarily need to even have a sales call. They're just
00:09:35.520 | ready. They want to see the product. If it works, they want to go test it. And Stripe
00:09:39.040 | really built for that. At the time, we used to talk a lot about arming the upstarts and
00:09:43.280 | really providing a product that helps support others, founders, and startups, and small
00:09:49.000 | business owners do whatever they need to do and not have all of the bureaucracy and all
00:09:53.680 | of the white tape.
00:09:55.120 | And that was something that was, I think, such an important and vital part of Stripe
00:09:59.400 | because it made it possible where, yeah, within a week, you can start accepting payments for
00:10:03.960 | your product, which is so much of the lifeblood of what proves out a company.
00:10:07.720 | So for those who are unfamiliar with what Stripe does, what does it do and how does
00:10:12.680 | it make money?
00:10:14.320 | Stripe started off being one of the first companies that made it really easy for any
00:10:19.060 | company in the world to accept credit card payments. Over the course of my time there,
00:10:23.640 | Stripe really evolved from being a pure credit card payments company to really providing
00:10:27.920 | a number of different financial infrastructure products, which also enabled you to move money
00:10:33.400 | between people or businesses, for you to open up bank accounts, for you to issue credit
00:10:40.360 | cards, for you to be able to set up subscription payments, fraud protection.
00:10:46.360 | So a lot of the core infrastructure, if you're thinking about now moving money, either between
00:10:51.200 | people or as a business.
00:10:53.220 | And that was really something that has unfolded and is the analogy of a lot of times when
00:10:57.240 | people talk about AWS, for example, it's just core to a company being able to run.
00:11:03.240 | So AWS is Amazon Web Services.
00:11:06.920 | And so I think for those who are familiar with FinTech and startups, Stripe is one of
00:11:11.840 | the largest private startups and it's not really a startup anymore.
00:11:16.440 | It's been around for a long time.
00:11:18.300 | At one point it rose to a almost a hundred billion dollar valuation during the boom in
00:11:23.560 | what 2020, 2021.
00:11:25.960 | And now it's kind of come back to about 50 billion.
00:11:27.880 | So that's still 10 X when you joined.
00:11:31.920 | So I'm curious, how long did you end up being at Stripe and with so much success with Stripe,
00:11:38.720 | why did you decide to leave?
00:11:41.320 | Great question.
00:11:42.320 | So I was there for three years from 2015 through to 2018.
00:11:47.200 | By the time I was making the decision about, you know, what to do next, the company was
00:11:52.080 | about 1,500, 1,600 people.
00:11:54.760 | It was a tough decision.
00:11:56.040 | I think, you know, I moved to San Francisco for Stripe at a time when also so much of
00:12:02.360 | my own social network were people at the company.
00:12:05.720 | And so it was fairly immersive in terms of, you know, how I spent my time, who I spent
00:12:11.380 | my time with.
00:12:12.960 | And they're really good, kindhearted people, very smart, hardworking.
00:12:18.400 | And I really enjoyed getting to know and building lifelong friendships with a lot of people
00:12:22.560 | that I worked with.
00:12:23.980 | So the decision to leave was actually even harder because of that.
00:12:27.880 | But ultimately for me, I known that, you know, the reason I had been excited to join Stripe
00:12:33.240 | at the beginning was because I thought it was a really great environment for me to learn
00:12:37.640 | a lot about a lot of different parts of running a company.
00:12:41.140 | And the things that I would learn the most in at that chapter when they're about 1,500
00:12:45.360 | to 1,600 people, and for that to grow to, you know, 3,000 or 5,000, the types of things
00:12:51.560 | I would learn would be less and less relevant to me actually starting a company one day.
00:12:57.220 | And so that for me was a really big driver for that was just realizing even though it
00:13:02.480 | was a great company doing very well, great environment, what I would be learning would
00:13:08.940 | just be less, you know, relevant to what I was actually more excited to do down the road,
00:13:13.700 | which was ultimately build my own company.
00:13:16.260 | Got it.
00:13:17.260 | That makes a lot of sense.
00:13:18.640 | Could you talk about the pay compensation, but you don't have to talk about your specific
00:13:23.620 | pay compensation, but how much were people getting paid in general for various ranks
00:13:29.580 | and how much of that was stock compensation?
00:13:32.520 | That's one question.
00:13:33.520 | And then the second question is when you leave a startup, what is the process like in terms
00:13:38.320 | of buying your options or RSUs?
00:13:41.580 | Yeah, great question there.
00:13:43.620 | So it's not uncommon for people to over time, especially as the company raises more money,
00:13:50.300 | has higher valuations for the stock compensation to get to almost as much as, you know, 70,
00:13:56.460 | 80, 90% of your total compensation.
00:14:00.260 | That's not true though at the time when it's granted.
00:14:02.620 | And so usually is somewhere in that, you know, 20 to 150% of whatever your salary is in terms
00:14:10.040 | of what you might be making from a stock compensation in that first year.
00:14:13.940 | What you're ultimately betting on is for that stock compensation value to grow because the
00:14:19.380 | company is doing well.
00:14:20.780 | And so that's also where there is such, you know, a lopsided nature to how equity compensation
00:14:27.260 | works.
00:14:28.260 | The other thing that's also important is because even though, you know, a company might grow
00:14:31.880 | from call it 10 billion to a 20 billion valuation, usually the impact for an individual on their
00:14:38.260 | equity compensation is actually more than the 2X because there's also going to be a
00:14:43.740 | buffer built into it, which is at the time when you're granted, your shares, you know,
00:14:48.460 | are not considered to be liquid.
00:14:50.420 | So that actually means that your shares are worth even less than what that last round
00:14:54.180 | is.
00:14:55.180 | So there's actually a lot of upside that usually is more than even just how much the valuation
00:14:59.020 | grows up by.
00:15:00.500 | Can you clarify that a little bit?
00:15:03.140 | So let's say I have $100,000 in stock options.
00:15:06.700 | It's worth $10 billion, it goes to $20 billion.
00:15:09.420 | Are you saying I should think that my $100,000 is worth more than $200,000 or less than $200,000?
00:15:15.500 | Usually it would mean that it's more than $200,000 because when your stock options are
00:15:20.340 | granted and they're valued at $100,000, let's say at a $10 billion valuation, your stock
00:15:28.020 | price that the investors paid was $1.
00:15:31.820 | But when you're holding that, actually when you pay for it, you won't be paying $1 because
00:15:37.300 | you can't actually sell.
00:15:38.740 | So that's what's called included, you know, the liquidity is taken into account for the
00:15:44.140 | value.
00:15:45.140 | So you as an individual, when you are granted that option, usually you'll be granted at
00:15:50.140 | a lower price, which might be, you know, if the investors paid $1, you might be paying
00:15:54.020 | $0.50.
00:15:55.020 | Okay.
00:15:56.020 | And that's pretty common?
00:15:57.660 | That's fairly common, fairly industry standard for valuation practices, because as an employee,
00:16:04.220 | you actually don't have as much flexibility to be able to sell.
00:16:07.380 | So because you can't sell, that means, you know, you have a discount.
00:16:12.460 | That's also why when companies get closer and closer to an IPO, that discount usually
00:16:16.220 | decreases.
00:16:17.220 | So, you know, any employee holding stock, it should get closer and closer to whatever
00:16:21.580 | the price an investor would pay.
00:16:23.860 | Hmm.
00:16:24.860 | Yeah.
00:16:25.860 | For folks listening, I'm sure many folks work at big tech companies or startups, and
00:16:31.420 | it seems very important for employees to understand what exactly they're getting and at what valuation.
00:16:38.020 | Do you have any advice for employees who want to join startups on what they should ask their
00:16:42.980 | managers?
00:16:43.980 | Absolutely.
00:16:44.980 | So one of the most important things to ask is what the last 409A price is, or said differently,
00:16:53.220 | what is the strike price of the options you're granted?
00:16:57.020 | That is ultimately, you know, what price are you paying in order to buy your shares?
00:17:02.860 | And that's something that a lot of times people don't ask.
00:17:05.180 | It's extremely important because that is ultimately, you know, as you think about how much money
00:17:10.420 | you have to pay to buy into the company, that's the amount, first off, that you need to pay.
00:17:15.060 | The other thing that's important is if you ever leave, you usually, the industry standard
00:17:19.480 | is that you get some number of months in order to then buy all of your shares.
00:17:24.480 | And so if, let's say the price is really high, then it might make it even harder for you
00:17:30.020 | to leave one day, or it might be a reason why you might stay longer.
00:17:34.060 | That's not uncommon, you know, for people to end up being in this situation because
00:17:37.700 | they didn't ask.
00:17:39.140 | The other thing, especially given the current landscape of startups, that I would highly
00:17:43.840 | recommend are for people to really deeply understand what were the prior fundraisers
00:17:50.760 | and valuations.
00:17:52.260 | Because right now we're in this really interesting time with startups where there are still a
00:17:56.460 | number of startups that raised at valuations one, two, or three years ago that were very
00:18:02.660 | high.
00:18:03.660 | Based on what the current multiples are, and multiples in terms of what is the revenue
00:18:09.540 | times a multiple equals, you know, the valuation of a company, based on what the current multiples
00:18:14.980 | are, they're much lower in the market nowadays.
00:18:17.700 | And so if you're someone joining a company and it was valued at $200 million, well, if
00:18:23.800 | an investor were to put money in today, they might not think the company is, even after
00:18:28.100 | it's grown, worth $200 million.
00:18:30.960 | And so that's where it really hits people who are joining the company, who might be
00:18:34.820 | in a situation where they are granted equity that isn't worth actually anything, potentially.
00:18:40.500 | Right.
00:18:41.500 | Yeah.
00:18:42.500 | It's just like if you're joining a company, you should put on your analyst hat and analyze
00:18:47.260 | the company's financials, expected growth, balance sheet, latest fundraising, and so
00:18:54.580 | forth.
00:18:55.580 | Super important.
00:18:56.580 | That's definitely what I've thought about in the past when I was working.
00:18:59.900 | And now maybe same thing in the future.
00:19:02.760 | In terms of leaving Stripe, because I'm assuming that you were paid quite well, did you ever
00:19:07.640 | do like a model where you said, well, if I stay at Stripe for 10 years, I'm going to
00:19:11.980 | earn this base salary and get potentially XYZ stock compensation, and then maybe I'd
00:19:17.500 | be set for life.
00:19:18.500 | How did you come up with that like financial decision to go leave Stripe and then join
00:19:23.540 | your own or start your own company?
00:19:26.260 | Great question.
00:19:27.260 | So for me, I definitely did think a lot about the fact that, you know, I would be leaving
00:19:33.960 | earlier, I would be leaving potential Stripe stock on the table.
00:19:38.720 | And ultimately, the thing that I thought about there, and this has actually been a guiding,
00:19:42.800 | you know, North Star for me, my whole career was the value of what I can learn will have
00:19:49.100 | a much bigger impact on my future earning potential than necessarily the dollar that
00:19:54.160 | I earn right now.
00:19:55.920 | That's been an important guiding factor, because actually, you know, when I even took
00:19:59.220 | the role in venture, for me, it was a role where I thought I would earn a lot more.
00:20:03.480 | I actually took a pay cut compared to what I could have earned at other job offers that
00:20:07.180 | I had.
00:20:08.180 | But I just thought that in a venture environment, I would just learn far more.
00:20:12.060 | Even when I was joining Stripe from a cash salary compensation perspective, it was a
00:20:17.540 | cut based on other opportunities that I had at that time.
00:20:20.820 | It was actually, you know, almost 40 to 50 percent lower from a cash compensation perspective.
00:20:26.440 | But I still thought it was worth it, because even, you know, an extra 20 or 40 or 50,000,
00:20:32.640 | when I thought about it, I was like, wow, it is a lot.
00:20:36.000 | But relative to the impact it could have on my future earning potential, it probably won't
00:20:41.960 | matter as much compared to if this opportunity I could learn, you know, twice as much or
00:20:47.640 | I had twice as much exposure to seeing how the best people in the industry do it.
00:20:52.720 | So for me, that's always been a really important part of framing, especially, I would say,
00:20:57.360 | like career growth in your 20s and 30s.
00:21:01.640 | And so that was actually something that, for me, guided that.
00:21:06.080 | And ultimately, at Stripe, like, yes, it was a much more known amount in terms of what
00:21:10.800 | that option could be if I stayed.
00:21:13.040 | But I thought I could just learn more and have the chance to do even more things hands
00:21:17.160 | on if I end up going to a smaller company.
00:21:20.520 | Right.
00:21:21.520 | So tell me or tell us about the path after Stripe.
00:21:24.720 | Yeah.
00:21:25.720 | So I ended up getting pretty lucky where one of the early investors in Stripe had ended
00:21:31.860 | up introducing me to one of the companies that I ended up going to afterwards.
00:21:37.080 | I pretty much had had a conversation where I was like, you know, I'm really looking for
00:21:40.080 | a much earlier stage team.
00:21:42.120 | And I really want to go to a company where I feel deeply connected to the mission of
00:21:46.760 | what the company is doing.
00:21:48.720 | Stripe was at a point where they were starting to build for larger enterprises, which is
00:21:53.040 | extremely valuable and important.
00:21:55.540 | But for me, I've just always been driven by more of the stories of individual humans and
00:22:00.180 | people and families.
00:22:01.640 | And so I knew I wanted to build a product that was ultimately a consumer product at
00:22:06.040 | the end of the day.
00:22:07.280 | I ended up joining this company named Even right around when they were 30 people initially
00:22:12.400 | joining as chief of staff.
00:22:14.060 | And then I stepped into an acting CEO role there.
00:22:17.280 | The company was really focused on helping individuals living paycheck to paycheck reach
00:22:21.220 | a point of financial stability.
00:22:23.520 | And I like to joke that I had the best values interview that any startup probably could
00:22:29.000 | have had because I ended up actually meeting my life partner and now my co-founder there.
00:22:35.040 | And we had both joined for the mission.
00:22:37.720 | Got it.
00:22:38.720 | And how long were you at Even?
00:22:40.640 | And how did that, I guess, journey and compensation compare to if you had stayed at Stripe?
00:22:48.120 | Yeah.
00:22:49.120 | So for that, because of the role that I was in, I was in a more senior role.
00:22:53.920 | We ended up selling the company to Walmart and won.
00:22:57.900 | And so from an acquisition and exit perspective, it was, you know, a pretty solid startup exit.
00:23:05.320 | We ended up selling the company into this big entity that is Walmart's new entrance
00:23:11.180 | into banking.
00:23:13.080 | And as I think about, you know, part of this is from an opportunity perspective, part of
00:23:17.960 | this from a compensation perspective, I think it ended up working out.
00:23:22.520 | The ultimate part, though, was that the type of experience that I had, because I was effectively
00:23:28.180 | the CEO's right hand, I ended up being able to further build, you know, the people that
00:23:33.040 | I got to know, really get to see firsthand how to operate at an executive level.
00:23:37.760 | You know, we were there as a company was about 30 people to over 120 people.
00:23:42.640 | And so the exposure and experience I got was one where I probably wouldn't have gotten
00:23:47.040 | an equivalent amount of exposure to kind of being firsthand making the decisions, being
00:23:52.280 | firsthand in all of the most important meetings as I would have had I stayed at Stripe.
00:23:57.480 | And so that experience was ultimately the most important thing for me ultimately getting
00:24:02.140 | the confidence to be like, oh, I think I'm ready.
00:24:05.360 | I don't think I actually have another startup that I want to go get more experience at.
00:24:09.560 | I think I've, you know, seen how some companies are built and there's no time like now and
00:24:15.200 | now is the right time to build a company like Plenty.
00:24:17.720 | Yeah.
00:24:18.720 | I mean, that's a great arc because I think joining Stripe in 2015 and then watching it
00:24:24.800 | 10x or more was kind of a really good move, right?
00:24:29.160 | Pretty lucky, pretty auspicious.
00:24:31.240 | And then joining even at 30 and then selling to Walmart, probably for a multiple of the
00:24:36.320 | valuation where you join at was also a good move.
00:24:39.320 | And so could third time be the charm?
00:24:41.680 | Well, it's been two times already.
00:24:43.360 | So let's talk about Plenty.
00:24:45.320 | When did you all start and how difficult or easy was it to come up with the idea to help
00:24:51.600 | modern couples manage their money?
00:24:54.080 | And also how difficult or easy was it to raise capital and get other people to believe in
00:24:58.600 | the mission?
00:24:59.600 | Yeah.
00:25:00.600 | So Plenty was started two years ago and it really started out of a lot of frustration
00:25:06.040 | that Channing and I had had when we started trying to merge our finances after we got
00:25:11.200 | engaged.
00:25:12.280 | We were trying to answer what felt like fairly straightforward questions like, where should
00:25:16.960 | we put our money?
00:25:18.360 | How much do we need for a house?
00:25:20.280 | What happens if we have two kids or three kids or four kids and what does that look
00:25:24.680 | like in terms of what we would need to support that?
00:25:27.780 | And the thing that was crazy was we were like, we're not the first ones to ask these questions.
00:25:32.480 | So many couples have asked these questions, are asking these questions.
00:25:36.940 | So surely there must be great products and solutions for this.
00:25:39.880 | The thing that was mind blowing for us was we tried every product and we're like, wait
00:25:44.320 | a second.
00:25:45.320 | Almost all of the products that we can see from the last generation of FinTech only really
00:25:49.120 | work for you to use on your own.
00:25:51.880 | They have all these, you know, I'm not going to name names here, but there's definitely
00:25:56.160 | companies that have joint products where both people can't even deposit.
00:26:00.440 | You have companies that offer, quote, family plans, but they don't even offer joint accounts
00:26:04.160 | and there's no shared visibility.
00:26:06.400 | So we started seeing all these broken holes where we were like, wait, we know that modern
00:26:11.080 | couples want to work together a lot more than the tools enable that right now.
00:26:17.020 | So that was a really big starting point for us.
00:26:19.900 | Another starting point too was we started, you know, meeting, we actually found this
00:26:23.700 | list of Forbes top 40 financial planners for millennials.
00:26:27.720 | And we were like, well, let's just see what that's like.
00:26:29.640 | Maybe that is a good solution for our generation.
00:26:32.800 | And after interviewing with about 20 of them as a prospective client, we just got fired
00:26:38.240 | up because we had people, what it felt like selling a snake oil where we were like, wait,
00:26:43.520 | we both come from a background in finance.
00:26:45.520 | You know, I have my CPA and my CFA Channing has a degree in finance and economics.
00:26:50.480 | And we were like, you're just throwing buzzwords at us to make it feel like we should trust
00:26:55.320 | you and pay you either thousands of dollars, a couple percent.
00:27:00.420 | You know, we had one person even try to pitch us on three percent of our annual income in
00:27:04.580 | order to work with them as a client.
00:27:06.760 | And this was one of the people on the top list too.
00:27:09.840 | And we were just shocked that we were like, this can't be the solution for people who
00:27:15.200 | are just trying to do the right thing with their money.
00:27:17.800 | It needs to be a lot more affordable.
00:27:20.600 | And it also is just a different service offering.
00:27:23.500 | People I think don't want to talk to humans to the same degree and say that every single
00:27:27.620 | question you have, you don't have the ability to answer it on your own.
00:27:30.800 | You have to talk to a human and email them.
00:27:33.580 | And then, by the way, also pay them, you know, five thousand dollars a year.
00:27:36.520 | Right.
00:27:37.520 | So that was a really big core for what started, you know, things.
00:27:41.600 | And then ultimately, one of the things that we also believe in deeply is over the course
00:27:44.740 | of the next 10 years, we believe that because of the last generation of fintech and especially
00:27:50.640 | fintech infrastructure, there will be a small number of companies that really challenge
00:27:57.160 | the Wells Fargo's, the Schwab's, the big banks in the U.S. and are actually able to
00:28:03.420 | challenge them because they've built a much better product offering that all works together.
00:28:09.400 | Your taxes are integrated with your investing, which is integrated with how you apply for
00:28:13.160 | your mortgage, which integrates with how you manage your day to day spending and saving.
00:28:18.580 | And we believe that will be built and aim to make plenty one of those companies.
00:28:24.160 | Awesome.
00:28:25.160 | So for 2024, let's say second half of 2024, what can plenty provide couples today?
00:28:32.320 | And where do you see the roadmap over the next three to five years?
00:28:36.880 | Great question.
00:28:37.880 | So right now, couples can come in and have one place where they can see what they have
00:28:44.220 | together as well as what they have on their own.
00:28:47.960 | We treat every partnership as a partnership plus two individuals.
00:28:53.080 | And so you have this visibility into not only all the accounts that you have not at plenty,
00:28:58.260 | but also your spending, your saving and investing and your income.
00:29:02.640 | From there, we know that one of the big drivers for couples and one of actually the most positive
00:29:07.660 | moments of talking about money is really talking about the goals that you share and want to
00:29:12.120 | work on together.
00:29:13.480 | So we offer plenty investment accounts so you can easily save or invest towards a home
00:29:21.000 | renovation, a home down payment, maybe for your kids to go to college for your retirement.
00:29:26.800 | And so we will actually help you stand up both investing and saving where our savings
00:29:31.280 | product today, you know, interest rates always change, but right now it's the 5.1 percent
00:29:35.480 | rate.
00:29:36.480 | And we also have a more advanced stock portfolio that we put together for you that uses individual
00:29:41.840 | stocks instead of ETFs in hopes that it ends up actually reducing future taxes that you
00:29:47.400 | might pay.
00:29:48.880 | And very much our mental model for all the investment products that we offer are really
00:29:53.200 | looking at what you would get if you worked with a wealth manager.
00:29:56.280 | But for most everyday families, they don't even know to ask for much less.
00:29:59.880 | They don't even know that it could be right for them or how to access it.
00:30:03.880 | So that's a bit of a framework for how we've thought about what products we will have as
00:30:08.160 | part of our upcoming launch.
00:30:10.120 | And then for the rest of this year, we're really excited to bring banking to the forefront
00:30:14.200 | as well, so you can also offer a plenty checking account as well as a savings account.
00:30:20.720 | And you will also be able to manage your taxes, too, from Plenty.
00:30:25.600 | Got it.
00:30:27.080 | Sounds like a lot is ahead and sounds really good.
00:30:30.280 | In conclusion, can we talk a little bit diving down deep into joining a startup?
00:30:37.320 | Because I know a lot of listeners here might also want to move to San Francisco or some
00:30:41.760 | big city and join a startup and leave their boring career behind where they're not learning
00:30:46.680 | much of anything and they're just doing the same old thing over and over again.
00:30:51.760 | What are your thoughts about joining a startup at various stages of funding?
00:30:56.640 | For example, pre-seed, I guess seed series A, B, C, D, and then I guess eventually IPO,
00:31:03.320 | which is not a startup.
00:31:04.960 | Yeah, so I would say this with, you know, very much a lot of awareness that I've been
00:31:12.720 | incredibly lucky with the companies that I have ended up joining.
00:31:17.360 | I think also one thing is at every step when I made the decision to join a startup, for
00:31:23.360 | me it wasn't just joining any startup or taking any job.
00:31:27.560 | I talked to a number of different companies and opportunities.
00:31:30.880 | I really evaluated every startup as if I were an investor who could only make one investment.
00:31:36.720 | And so I don't think all startup jobs are necessarily equal.
00:31:41.120 | I think it's helpful to have a foot in the door for your initial startup, if especially
00:31:46.520 | if you're moving from another city where there might not be as much of a startup or tech presence.
00:31:52.320 | But ultimately I would say very early on, it matters a lot if you're at a company that
00:31:58.520 | has seen growth.
00:32:00.120 | And so being very analytical, even if it's necessarily, you know, the perfect role, I
00:32:05.320 | would take not having the perfect role at a startup that is growing quickly any day
00:32:10.920 | over "the perfect role" at a company that isn't growing.
00:32:14.880 | Because what ends up happening is you end up spending a lot of your time and a lot of
00:32:18.720 | the experience you gain is not actually solving growth problems.
00:32:23.240 | And it also is a bit more of like a strange dynamic where at Stripe, it was so collaborative
00:32:27.560 | because the company was growing so quickly, where everyone was just trying to help each
00:32:31.560 | other because ultimately we were trying to help the company and everything, like we needed
00:32:35.720 | all hands on deck.
00:32:37.360 | And what I've also seen is sometimes when people join companies that don't grow as much
00:32:41.960 | or aren't growing at all, it ends up actually creating a lot more of pressure where instead
00:32:47.000 | of everyone pointing forwards, you end up having a lot more internal politics and a
00:32:51.560 | lot more internal dynamics because ultimately it's not solving the problem that, you know,
00:32:55.680 | the company isn't growing or there's other issues that are bigger with the company.
00:32:59.680 | So especially if you're earlier on in your career, I'd recommend like say yes to a seat
00:33:04.800 | on something that is growing quickly.
00:33:06.800 | I think my original title was like a sales analyst accountant.
00:33:13.720 | It was like a hodgepodge title, but it was like, I'll take whatever seat and I'll just
00:33:17.640 | once I get there, like I'll do whatever we need, which I think is absolutely the mentality
00:33:21.840 | that is, you know, helpful and you also learn the most in while you're joining something.
00:33:25.760 | Got it.
00:33:26.760 | Well, it's been a great journey, Emily, and I wish you best of luck with plenty.
00:33:32.080 | Thanks again for joining the podcast and sharing your wisdom about the startup world.
00:33:36.120 | Thank you so much for having me, Sam.
00:33:38.240 | All right.
00:33:39.240 | Take care and we'll speak again.
00:33:40.240 | All right, everyone.
00:33:41.240 | If you enjoyed this podcast, I'd love a share, subscribe and a positive review.
00:33:44.640 | It helps keep me going.
00:33:46.680 | Every single episode takes hours and hours to produce.
00:33:49.540 | If you want to keep in touch, check out the Financial Samurai newsletter at FinancialSamurai.com/news.
00:33:56.640 | Talk to you all later.
00:33:57.440 | [Music]