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414: Sagewell Financial with Sam Zimmerman

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Sam Zimmerman is CEO and Co-founder of Sagewell Financial. Sagewell is building a banking platform for the needs of folks who are trying to retire and live off their savings and income as intelligently and as well as possible.

Chad talks with Sam about deciding what their first product should be and what they would be bringing to market, finding the right partners, and minimizing risk to make a business and a product that works.

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Transcript:

CHAD: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Chad Pytel. And with me today is Sam Zimmerman, CEO and Co-founder of Sagewell Financial. Sam, thanks for joining me.

SAM: Thanks so much for having me, Chad.

CHAD: I've been following along with Sagewell Financial for a little while now, given our cross-histories and the fact that we worked with a few companies that you've worked at in the past. So I'm aware of what Sagewell Financial is, but I'm not sure that all of our audience is. So I think a good place to start would be by giving folks a little bit of an intro into what Sagewell Financial is, and then we'll touch on the founding story and go from there.

SAM: Awesome. So, in a sentence, Sagewell is building the digital banking that our parents deserve. To expand on that even more, America's retirees are a really interesting and important and powerful demo in American culture at large. There are 56 million Americans on a fixed income. And last year in venture capital, nearly $100 billion went to fund financial technology companies rewriting all of finance. And of that 100 billion or a little under, less than a fraction of a percent went to America's seniors.

And so we are trying to build banking from the ground up for the needs of folks who are living on a fixed income who are in their golden years and aren't thinking about that new job or making new money. We're building a bank for folks who are trying to retire and live off their savings and their income as intelligently and as well as possible. And that looks really different than the bank that a millennial or a Gen Z user might have.

CHAD: So that's really interesting. Right or wrong, what are the reasons that this historically hasn't been a target demographic for investment?

SAM: So the prevailing assumption among venture capitalists was (We're changing that and hopefully changing that quite quickly.) was that retirees aren't open to changing. Beyond that, they're also not technically sophisticated. These folks don't know how to use a phone or aren't open to a bank that might not have any physical branch. They are set in their ways. They're not going to move branch, or they're barely going to watch a new TV show.

A lot of folks who are trying to talk...imagining a grandma or a grandpa was really what the venture capitalists are drawing on often when they're thinking about why a senior wouldn't expect to have a bank with all the new features that the millennial might.

CHAD: Well, that one is certainly changing, especially as the venture capitalists get older themselves. They probably realize that that's an outdated notion in terms of the technical aptitude or familiarity of that audience, right?

SAM: Exactly. And it's a fascinating moment. There are 10,000 boomers who turn 65 each day in America, about 4 million folks each year. And those folks were about 40 whenever the.com boom passed. They've been using email. They have XE and PayPal. And importantly, why we're building this company now is that COVID changed seniors' digital lives more than anyone else. ARP reports how 70% of all American retirees know how to use Zoom and video conferencing software nowadays.

Across the stack of digital goods and services, seniors were actually the group that was most moved online. And so, from where we sit as entrepreneurs, we saw a massive market, an exogenous effect creating a disproportionate opportunity. And so we began designing and iterating on and understanding our user to build a product that met those needs with this massive and growing market.

CHAD: Banking is a highly regulated complex space. And I imagine from day one you're looking at that and saying, "Well, we might want to do everything eventually, but doing everything is going to be difficult." So what was the process you and your co-founder and the team around you used to decide what the first product should be and what you were going to bring to market?

SAM: Our founding team spent almost nine months in user interviews and user research across what one director of finance at Capital One called geriatric finance. We talked to hundreds of folks, and a lot of our assumptions about what the simplest or most low-trust or quickest to use service might be were actually totally turned on their head in a really interesting way.

Another reason why venture capitalists aren't so confident you can reach this demo is a couple of companies have come before us, and a lot of them followed, in financial technology, a Mint-like model where you log in, and you share your various bank credentials. They pull your credit card transactions and bank transactions. And one of the really surprising things in our hours of user interviews was that that model was really unpalatable to this demo. They actually thought it was a lot higher trust to share bank credentials than it was to actually open an account.

And so we began thinking, what's the highest engagement, most common accessible feature that our demo is familiar with? And that's already broadly online. And let's start there. And the original insight came with a woman she was from Pennsylvania, and we were talking. We built this kind of mint.com-type prototype to try to help imagine banking for her needs without this high trust checking account. And she was like, "Oh." She was aghast that we were even considering asking for her bank credentials.

We heard that, and then we said, "All right, no worries, no need to do this product demo." And then she was like, "But I really love Chime, and I really love Chime's checking account." And we were like, "Wait, you have a digital bank account?" And she's like, "Yeah, I love Chime." And it was this moment where thinking about our user, what trust meant to them, what was familiar to them, and what being online meant to them opened the floodgates and helped us really understand this user and what that first product needed to be.

And so our initial product is a checking account. It's got a variety of senior-specific features around and enabling it. And it's built incredibly excessively to be available to folks who use technology in all sorts of ways. But we started with the basics because that's what our members are most familiar to and most expect.

CHAD: So you say in the fine print on the website that Sagewell is a financial technology company and not a bank, and your banking services are provided by a partner. What was involved in actually bringing that online, finding the right partner, implementing the features? What did that look like?

SAM: Yeah, it is an incredible time to be building any sort of banking in America around the world. So to that point earlier, $100 billion was pumped into financial technology companies. And so as a result, there are so many companies and so much innovation happening in banking and fintech broadly. And so starting and figuring out what vendor to work with was actually what our strategy from a banking and regulatory perspective was. And in turn, what vendors and in-house technology we needed to build was one of the hardest initial challenges that I've ever had to face in building a company.

It is still, despite what many...you'll see a lot of ads, you know, "Have a card online in minutes." It is still in today's day and age quite an achievement to build banking and get it online, and servicing your customers in a scalable and sustainable way. And so we spent a lot of time early on in the architecture and vendor selection process and product strategy process thinking about what vendors to go with; what we were going to build in-house. And before ultimately breaking ground about three months after we began, we set the product itself, which was going to be a checking account for retirees.

CHAD: What were the factors that went into choosing the partner that you ultimately chose?

SAM: Beyond your standard enterprise vendor selection, we wanted to make sure that it was secure, and we wanted a specific set of features. In our space, there are about six different companies that provide what's called Banking as a Service technology. And so that was one of our key vendors is the technology company that works with the bank to allow us to open checking accounts, fund accounts. And most of those companies have been around for only a few years. And so their products themselves are hardening and being built.

And about $200 million I would say has been invested in those companies last year. And so we wanted one that was well-capitalized. We wanted one that had not had any IT security issues. We wanted the underlying bank to be aligned in our mission. Retirees have a variety of specific financial needs. A lot of our product development involves working very closely with the bank. And so, we needed to make sure that the bank itself that they worked with was on board.

And lastly, we talked to other customers, and that was ultimately the most valuable thing in our experience and not just the customers that they refer you to but the customers who have left for one reason or another. Those were the major factors that we chose in our Banking as a Service provider. And then, beyond that, that's one piece of the puzzle. In our bank tech stack, we're looking at around 15 different partners across all parts of banking. And that's the largest and most important one. And those were the criteria we used to select.

CHAD: I often say when I'm looking at building a product or service, and we look at those integration points with external vendors, it is one of the riskiest parts of building a product because you're not in control of it. So from a business perspective, it's risky. But also, from a technology perspective, that's where estimates can get out of whack.

And things can work not like you're expecting or like the documentation said or just surprises crop up along the way. Or when something goes down, your product is broken. And your entire product [laughs] basically is built on those vendor relationships. So, how do you minimize that risk and work in that environment to make a business that works and a product that works?

SAM: [chuckles] I suppose the answer is with a lot of prudence, thoughtfulness, and care at a high level.

CHAD: [laughs]

SAM: I was actually just talking with a CTO friend of mine just talking about how in a lot of startups, one of the skills that I most ask of engineers and engineering leaders early on is vendor selection and how I hadn't seen an interview process that really helped get at that. It's a core part of a lot of technologists' jobs and particularly a lot of engineering folks' jobs. The API docs looked good but did he test it or evaluate it? Was there a third-party tool you could have used instead of building in-house?

Those are the sort of questions that a lot of times early-stage startups are answering all the time. And I had yet to see an interview that got at that. So it's a really shrewd point and one that I hope that as technologists and particularly early-stage startups become more about really going deep in one area and then leveraging third parties elsewhere, I hope that we start actually hiring and developing criteria to do that with the people that we assemble.

I think the first part what I would say is we described a little bit about the risks. We went through a risk mitigation exercise, which smells very enterprise-y. It's kind of the sort of thing that you would expect exists in some massive waterfall with a Jira board mainframe computer but just listing like, here's this integration. If this were to happen, what would we do? If the API went down, what control do we have, or how could we minimize the impact on our customers?

That exercise across some of our biggest integrations helped us select and take on the risks we wanted and avoid the ones we couldn't. So there was a lot of conversation about the sorts of failures we could put up with and how we could put up with them, and the sorts of failures we couldn't. And then really testing for the ones we couldn't to make sure that we were making as good a choice as possible.

Despite that thoughtful answer, it was the best we could do. I would say that, particularly in a space that's as fast-moving as Banking as a Service, I would say that a lot of it is still that soft skill, that relational conversations with other teams and folks and whether you trust the team that you're trusting to execute and build what they said they're going to build and that hiring skill but also a good bit of luck as well.

CHAD: So correct me if I'm wrong, but up until Sagewell, where you're CEO, you had been CTO of the other companies that you founded and worked at. Is that right?

SAM: Yeah, that's correct.

CHAD: So, what has the change to being CEO instead of CTO been like for you personally? And was that choice clear from the beginning with Sagewell?

SAM: So far, it's been incredibly rewarding. I would say in between startups; I actually volunteered at an organization called PathCheck. And while my title was CTO, the scope of that included partnerships, vendor negotiations, CISO exercises, product. It was a pretty expansive CTO role. And I found myself really energized by the breadth and the ability to work with even more really talented, thoughtful experts in their own domain and empower them to do more. And so I knew in my next role, I wanted more of that breadth.

There's an essay that classifies folks as foxes who can do a little bit of everything or hedgehogs who can do one thing really well. And I'm a super fox. [laughter] I love doing lots of things. And so CEO to me is just like an opportunity to...it's maximizing breadth and maximizing difference of experience. And I transitioned, I'd say, from a normal CTO role to a beefy CTO role to making CEO a pretty natural step from there.

CHAD: And your co-founder is named Jeff Wright, and he's the COO. How did you meet him and get started with Sagewell?

SAM: Jeff and I, it's been wonderful. I was trying to figure out how I was going to get engaged in pandemic work in April of 2020 after leaving my last startup while it was being sold to Capital One. And I was talking with a founder friend of mine, a guy named Ty Harris, who is the CEO of an Insurtech company called Openly. And he was previously the CTO at Liberty Mutual. And Ty and I had a couple of lunches and conversations, and I was talking to him about how it is getting involved in COVID stuff and how I was ultimately my species as an entrepreneur, and I was going to be building something again.

And he connected me with Jeff, and Jeff and I touched base quickly in April. And it was a little bit like a frog in the pot sort of situation where it started like, yeah, maybe we could build a company. Let's riff on some ideas and see what's out there. And it was a really, really natural progression from August to a couple of evenings, maybe a Saturday call or two, to most evenings and definitely a Saturday to oh, man, when should we transition?

CHAD: You were both working full time on other things at the time. You were working with PathCheck.

SAM: Yep, exactly. And so he was the CPO at a company called Plymouth Rock, and I was working at PathCheck. And not to go into PathCheck's story too much, but PathCheck was largely deploying a research technology, the Google and Apple Exposure Notification protocol. And it became clear that most of the states that were going to do anything were already going to do it. And so, it was natural to start thinking about what was next in August and September. And so, as my species does, that then became the night and weekend project to figure out what's next.

CHAD: So you mentioned that this is a space that is typically not strongly funded. So was that a challenge for you as you were getting started? How did you get that initial, you know, where did your initial funding come from? And I know you recently raised, at least it was announced, 5.3 million in January. So what was the transition from those early days? Where did the funding come from to ultimately getting the investment in this last round?

SAM: Jeff and I worked in the fall of 2020, met our CTO, Chris Toomey, in November actually from connection through a friend. Early on, we were a team with a demo. We really knew that we cared about seniors, and our background is in financial services. We were trying to think of a new product for seniors and so a financial product for seniors. And so, around January, we sharpened our pencils on the user research side of things and the product side of things. And once we had a clearer sense of the product direction we wanted to take, ultimately building banking for retirees, we began the fundraising process.

CHAD: So were you essentially self-funding at that point?

SAM: Yep. So we were self-funding from January-ish till May. I find that skin in the game to be… I wish I was the sort of founder who could think about flawless ideas without a little pressure. But in my experience, it's actually been where unless I jump in, unless I can have a little bit of pressure, my ideas aren't often as refined as I'd like. And so Jeff joined it full-time in February. And then we fundraised through April, closing a 1 million pre-seed, which is pretty common in fintech.

Most financial technology companies the banks won't talk to you until you have at least a million dollars in funding. And so we raised the money we needed from...and who did the money come from? It came from Point Judith Capital, who actually had invested in Ty, the guy who connected us, with his company Openly. So we had our initial conversation with David, who's been absolutely wonderful at Point Judith Capital.

And also, Jeff and I knew that innovating for a vulnerable population, ultimately retirees, meant that we wanted to have folks from the beginning who represented the seniority and seriousness with which we are taking our work. And so the second investor who in between the two of them took most of that million was Crossbeam and Raj Date at Crossbeam, who's the former Deputy Director of the U.S. Consumer Protection Bureau. We really wanted folks around the table who knew what innovation looked like and fintech innovation like David, as well as folks who understood the world of government and finance like someone like Raj to innovate thoughtfully with this demo.

CHAD: Was it difficult to get those funding rounds?

SAM: The first one? Yeah, the first one was about two months. I thought it would have taken about a month. The second one the market is pretty crazy right now. And I would say between my first company and my second, it used to be that you'd set aside six months to fundraise, and so I'd prepared for a six-month fundraise. Started kind of in early October two weeks in, and they were like, "Wow, you've already been in the market for two weeks?" [laughter]

And I was like, what? I was totally off base in terms of what was the new normal. Ultimately, that round came together in about a month and a half as well. And so we had a lot of interest. The second round that 5.3 million went from not a ton of interest to tons of interest and lots of folks around the table and having to push folks out or turn folks down pretty quickly. The first round, I would say for a pre-seed, one to two months given that the idea was hardening, sounds about right.

The second one was about one to two months but was a little...a lot of people would get excited by the market; they'd get excited by the team. And then they'd say, "You can't get a senior to open up a bank account," and then they'd come back. And then we found one believer alongside David and Raj, who had been with us. And once we got the folks at 25Madison and Merrill, especially, the rest of the round came together really quickly.

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CHAD: Given that you were able to put together a round quickly, how do you decide ultimately not to take even more money? What are the factors that go into deciding how much you're trying to fundraise and how big the round is going to be? And is there pressure as you're doing that to maybe go even bigger?

SAM: Yeah, we had, I would say maybe seven and a half million dollars interested. And ever since we've closed, we've had multiple firms who are interested in a new round of capital. The market is really, really quite founder-friendly right now. I think ultimately, for any founder, what you're trying to do is create as much value with as little capital as possible. That's ultimately the game that you're trying to play now.

For a little baby company, it's often really hard to figure out how much money or how much value you'll be able to create over what amount of time. There's so much to figure out. There are so many bets and learnings and risks that it's often very hard for a company to say, with $5 million, I'll create $20 million in value. So ultimately, if you're a founder, you're incented to give away as little of the company as possible and create as much value from that.

And so when we were doing our modeling, we actually thought that it was somewhere closer to four of what we needed to create the amount of value needed to raise our A. And we ultimately bumped it up to 5.3. And there's a good bit of advice you hear a lot among founders that raising a bit more than you think is prudent, and anyone who has managed a budget knows how that can go. So we ultimately did go up to 5.3.

But taking more would have meant that we were paying a premium where we could get that million dollars maybe in a year's time, and we'd be giving away a quarter-point or a half a point of the company for that million where we might be giving away 1% or 1.5% of the company now. So it's all about creating as much value with as little money as possible. And it's easy to get lost in the big rounds and the big numbers. But ultimately, it's pretty simple math.

CHAD: And correct me if I'm wrong, and this is a question as much as a statement. So to reiterate, the rounds you're talking about are seed rounds. And so traditionally, what that means is that the majority of work that you have to do is just making the product. But in the space you're in, there is a point in time where you've made the product, and you've shown the traction, so what you have becomes more valuable.

And so it might be that the next round, which is maybe a Series A, a significant portion of that capital would be spent on something else like marketing or sales teams and that kind of thing. And you're growing beyond just the product development at that point. Is that how you're thinking about this, or am I wrong?

SAM: So it's funny that it's really changed the names. The round size what they mean has changed more in the last two years than ever before, and I would say that, particularly in fintech, because fintech has a number of unique challenges. So I would say that that $1 million round that we raised in May that was really about building a very basic product, a very truly minimally viable acceptable product.

And then the seed round in fintechs is often about getting to product-market fit or just demonstrating you can reach your end consumer or target user. In fintech, it's often not quite as much tied to a certain amount of revenue at that stage. It's often about just demonstrating that you can get to that user, and that's because, in financial technology, the cost to acquire is often quite high.

And so for a company that only has raised, say, a $5 million pre-seed because of the gravity, because it often costs hundreds sometimes thousands of dollars depending upon the market to acquire a specific user, the math is such that you're just not going to have that many users, and you're not going to be able to get to a certain amount revenue. And so often in fintechs, 1 million gets you...that pre-seed gets you that initial product. The seed is about demonstrating that you can scalably get to that end user.

And then the series A is really about blowing that out and starting to exploit that marketing and acquisition machine that you've been building to start creating revenue. That's a little bit industry-specific. Other industries will have similar or different terms. And depending upon what sort of branding a firm might want for the round, you also might hear $100 million pre-seed. You hear those things as well. It's a crazy time to be building a company.

CHAD: So you mentioned Chris Toomey, who's the CTO of Sagewell, and he was previously at thoughtbot. As a prior CTO, what were some of the things you looked at in terms of finding Chris and deciding he was the right one to join your team as CTO? I imagine your standards were pretty high.

SAM: Yeah, and Chris met them quite happily. As a CTO transitioning to CEO, I think you have to understand your strengths and weaknesses as a CTO as well as the learning curve that you might have stepping into your new role as a CEO. And I would say that one of the fortunate things is that Jeff, my co-founder and COO, we actually have a pretty unique set of skills that can span a lot of different domains.

And so I would say that looking at Jeff, Chris, and myself, we really had to make sure we had our bases covered to build the financial and technology product we needed. I would encourage folks building a company early on to really think about your strengths and weaknesses, your founding team's strengths and weaknesses.

And as I was getting to know Chris, kind of the initial handshake agreement starting to build and prototype various solutions, I think that I was particularly impressed and looking for someone who was willing to have a deeply experimental and MVP mindset while managing the risks of working with a vulnerable population. And so over the course of December through March or April, in dealing with and spinning up a couple of different prototypes with radically different product strategies and end products, I was able to see how Chris was able to be mature and shrewd about where he could cut corners, where he couldn't cut corners and then execute accordingly.

It's funny, Chris and I were talking at our one on one a week or two ago. As a CTO, I know a little more of what's possible. I know if I come in and say, "I want the Taj Mahal," I know you'll get walked back down. Chris and I over the past year...I often come to Chris, having already teared down my Taj Mahal. And I'm like, "Well, Chris, what I really need is one little specific problem." And Chris and I actually set a goal between us that I actually kind of come to him asking for the Taj Mahal next time [laughter] or not next time but sometime in the next year.

Because I think one of the things I've had to check or do in CEO is let Chris do CTO's job and not internalize all the time his voice and concerns but actually put forth a vision and not be afraid about the fact that it isn't something that we can get to market in a week or that we can't ship in three or four weeks’ time, which is an interesting contract that I think we've developed and an interesting growth area. And it's my job to throw out bigger ideas, not to be the one who tears them down all the time, which is fun, and I enjoy doing that with Chris.

CHAD: Yeah, that's an interesting perspective. And I often even working with clients and consulting want that because if you're only getting the small pieces all the time, you cannot be privy to the big picture of what we're aiming for. And that will often lead you to maybe not taking everything into account, either that's on the roadmap or down the road. Or realizing, oh, you're disappointed now, but that's because I didn't know that you wanted to do this. If I had known, then we could have done this in a different way or something like that. And so, getting a sense of that big picture is often important.

SAM: Yeah. And it's a fun, I'd say...yeah, and growing with Chris and figuring out that he's the right person for the role as a CTO turned CEO means kicking off the ladder and actually just stepping into my role and letting him do his, which has been a fun contract to establish.

CHAD: So, did you work with Chris as a contractor before committing to him as CTO?

SAM: Yeah, we were in a consulting relationship. I think Chris was politely under billing. And the pretext is always that this was something that we were really aiming to build a company together, assuming everything worked out across Chris, Jeff, and I. And so, he did start in that capacity. And then I'm trying to remember the exact timelines. Sometimes the paperwork is well after the actual agreement whenever you're creating these companies. But in a few months’ time, definitely by July and probably by May, we were building the company and off to the races.

CHAD: Now, is that a path that you would recommend to other founding teams looking for a CTO is to not commit early to really make sure that you work well with someone, maybe through a contracting relationship first?

SAM: Yeah, I think ultimately, if you're going to be going on a journey, a decade long journey, a lifetime-long journey, through highs and lows, I think the best way for everyone to know what they're getting themselves into, the excitement, and the reward, and the aches, and the pains and the sleepy [inaudible 33:31] in the morning is by working together, and I don't think there's a shortcut. In this case, it depends a lot on the situation. It depends if folks are in a position where they cannot take pay. It depends on whether nights and weekends are free or they have flexibility in their other roles.

But generally speaking, I think that ultimately, you're trusting, and your founding team is going to be taking so many risks together that you want to go in as eyes wide open as possible and have removed as much founding team risk, disagreements, misaligned working styles, misaligned visions, or preferences as possible. My coach used to say that that's the number one reason why companies at the seed stage fail is management teams and founding teams.

And so as you're thinking about building your company, and I can't emphasize this enough, mitigating and removing founding team risk, however possible, with consulting being one of them and navigating a tough conversation or two being another, is absolutely core to removing as much risk as possible for your startup.

CHAD: That's great advice. And just like you and Jeff had a time of working together before you actually started a company together, I think it's great advice to try to find ways to do that with other early members of the team too because it's a big commitment, and you want to make sure that you get it right.

SAM: Exactly.

CHAD: Well, you've reached sort of the pinnacle of having now someone on your team that used to work at thoughtbot. I think I'd be remiss if I didn't point out that we have another podcast at thoughtbot; it's called The Bike Shed. And Chris started as a host on that show while he was on thoughtbot, and he continues that to this day along with Steph Viccari, who's a team lead at thoughtbot.

And so if people are interested in hearing about Chris' work now at Sagewell and following along with the team and the work that he's doing there as well as the work we do at thoughtbot, people can check that out at bikeshed.fm. Sagewell is not a client of thoughtbot. But you've worked with thoughtbot before as a client twice, right?

SAM: Yeah, exactly, both at my first company Freebird, which was sold to Capital One, and at PathCheck, the non-profit I worked at.

CHAD: So you specifically, I assume, then made an effort to recruit from thoughtbot when you started Sagewell. [laughs]

SAM: I would say I know and love the way that thoughtbot approaches building software. And I know and love the people that I've worked with from thoughtbot. And I would say that it was as much a feature of being in the same communities as it was specifying a specific group. But you guys have created a great culture. [laughs]

CHAD: I'm just kidding. I didn't actually think that that was the case, but I can guess a lot of the benefits of working with someone who's worked at thoughtbot before because of the level of experience and the level of skill and communication and everything that people at thoughtbot have. But I'm curious, what if I turn that around? Is there a downside to hiring someone who worked at thoughtbot previously to your team?

SAM: So one of the things that I love about, particularly early on, we have a hire that we just made recently. She worked at a senior living facility for four or five years and then worked at Wells Fargo for four or five years. And before, we had a bunch of fears, and this new employee listed five or six totally different fears than we ever would have thought of. And so now we have way more fears. And part of that can be unnerving, and part of that can be challenging.

And I would say that one of the challenges of working with a team that builds software in such a clear culture is that you might not get all the fears. You might not get certain sorts of diverse perspectives or headaches because of a particular way that product and engineering are conceived. And so one risk...it’s kind of the unknown-unknown sort of situation, but it's real in startups which is I think that making sure you have diverse perspectives across the domains where you need to be deeply an expert for folks who are very similar to you is a major risk.

CHAD: That's great. Well, Sam, thanks for stopping by and sharing with us. I really wish you and Sagewell and the entire team all the best.

SAM: Awesome. It was wonderful talking.

CHAD: And if folks want to find out more about Sagewell Financial or follow along with you or get in touch with you, where are all the best places for them to do that?

SAM: sagewellfinancial.com is our email. And if you or your parents are interested in what we're building as a customer or a member, you can sign up there. If you'd like to reach me, I'm mostly on Twitter following cute animals and occasionally a good tech post @Ferrum_of_omega. And if you'd like to contact our company, you can just go to /press and fill out the form there.

CHAD: Awesome. And you can subscribe to the show and find notes for this episode along with a transcript of this episode and all past episodes of this season at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. And you can find me on Twitter @cpytel.

This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks for listening and see you next time.

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Sam Zimmerman is CEO and Co-founder of Sagewell Financial. Sagewell is building a banking platform for the needs of folks who are trying to retire and live off their savings and income as intelligently and as well as possible.

Chad talks with Sam about deciding what their first product should be and what they would be bringing to market, finding the right partners, and minimizing risk to make a business and a product that works.

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Transcript:

CHAD: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Chad Pytel. And with me today is Sam Zimmerman, CEO and Co-founder of Sagewell Financial. Sam, thanks for joining me.

SAM: Thanks so much for having me, Chad.

CHAD: I've been following along with Sagewell Financial for a little while now, given our cross-histories and the fact that we worked with a few companies that you've worked at in the past. So I'm aware of what Sagewell Financial is, but I'm not sure that all of our audience is. So I think a good place to start would be by giving folks a little bit of an intro into what Sagewell Financial is, and then we'll touch on the founding story and go from there.

SAM: Awesome. So, in a sentence, Sagewell is building the digital banking that our parents deserve. To expand on that even more, America's retirees are a really interesting and important and powerful demo in American culture at large. There are 56 million Americans on a fixed income. And last year in venture capital, nearly $100 billion went to fund financial technology companies rewriting all of finance. And of that 100 billion or a little under, less than a fraction of a percent went to America's seniors.

And so we are trying to build banking from the ground up for the needs of folks who are living on a fixed income who are in their golden years and aren't thinking about that new job or making new money. We're building a bank for folks who are trying to retire and live off their savings and their income as intelligently and as well as possible. And that looks really different than the bank that a millennial or a Gen Z user might have.

CHAD: So that's really interesting. Right or wrong, what are the reasons that this historically hasn't been a target demographic for investment?

SAM: So the prevailing assumption among venture capitalists was (We're changing that and hopefully changing that quite quickly.) was that retirees aren't open to changing. Beyond that, they're also not technically sophisticated. These folks don't know how to use a phone or aren't open to a bank that might not have any physical branch. They are set in their ways. They're not going to move branch, or they're barely going to watch a new TV show.

A lot of folks who are trying to talk...imagining a grandma or a grandpa was really what the venture capitalists are drawing on often when they're thinking about why a senior wouldn't expect to have a bank with all the new features that the millennial might.

CHAD: Well, that one is certainly changing, especially as the venture capitalists get older themselves. They probably realize that that's an outdated notion in terms of the technical aptitude or familiarity of that audience, right?

SAM: Exactly. And it's a fascinating moment. There are 10,000 boomers who turn 65 each day in America, about 4 million folks each year. And those folks were about 40 whenever the.com boom passed. They've been using email. They have XE and PayPal. And importantly, why we're building this company now is that COVID changed seniors' digital lives more than anyone else. ARP reports how 70% of all American retirees know how to use Zoom and video conferencing software nowadays.

Across the stack of digital goods and services, seniors were actually the group that was most moved online. And so, from where we sit as entrepreneurs, we saw a massive market, an exogenous effect creating a disproportionate opportunity. And so we began designing and iterating on and understanding our user to build a product that met those needs with this massive and growing market.

CHAD: Banking is a highly regulated complex space. And I imagine from day one you're looking at that and saying, "Well, we might want to do everything eventually, but doing everything is going to be difficult." So what was the process you and your co-founder and the team around you used to decide what the first product should be and what you were going to bring to market?

SAM: Our founding team spent almost nine months in user interviews and user research across what one director of finance at Capital One called geriatric finance. We talked to hundreds of folks, and a lot of our assumptions about what the simplest or most low-trust or quickest to use service might be were actually totally turned on their head in a really interesting way.

Another reason why venture capitalists aren't so confident you can reach this demo is a couple of companies have come before us, and a lot of them followed, in financial technology, a Mint-like model where you log in, and you share your various bank credentials. They pull your credit card transactions and bank transactions. And one of the really surprising things in our hours of user interviews was that that model was really unpalatable to this demo. They actually thought it was a lot higher trust to share bank credentials than it was to actually open an account.

And so we began thinking, what's the highest engagement, most common accessible feature that our demo is familiar with? And that's already broadly online. And let's start there. And the original insight came with a woman she was from Pennsylvania, and we were talking. We built this kind of mint.com-type prototype to try to help imagine banking for her needs without this high trust checking account. And she was like, "Oh." She was aghast that we were even considering asking for her bank credentials.

We heard that, and then we said, "All right, no worries, no need to do this product demo." And then she was like, "But I really love Chime, and I really love Chime's checking account." And we were like, "Wait, you have a digital bank account?" And she's like, "Yeah, I love Chime." And it was this moment where thinking about our user, what trust meant to them, what was familiar to them, and what being online meant to them opened the floodgates and helped us really understand this user and what that first product needed to be.

And so our initial product is a checking account. It's got a variety of senior-specific features around and enabling it. And it's built incredibly excessively to be available to folks who use technology in all sorts of ways. But we started with the basics because that's what our members are most familiar to and most expect.

CHAD: So you say in the fine print on the website that Sagewell is a financial technology company and not a bank, and your banking services are provided by a partner. What was involved in actually bringing that online, finding the right partner, implementing the features? What did that look like?

SAM: Yeah, it is an incredible time to be building any sort of banking in America around the world. So to that point earlier, $100 billion was pumped into financial technology companies. And so as a result, there are so many companies and so much innovation happening in banking and fintech broadly. And so starting and figuring out what vendor to work with was actually what our strategy from a banking and regulatory perspective was. And in turn, what vendors and in-house technology we needed to build was one of the hardest initial challenges that I've ever had to face in building a company.

It is still, despite what many...you'll see a lot of ads, you know, "Have a card online in minutes." It is still in today's day and age quite an achievement to build banking and get it online, and servicing your customers in a scalable and sustainable way. And so we spent a lot of time early on in the architecture and vendor selection process and product strategy process thinking about what vendors to go with; what we were going to build in-house. And before ultimately breaking ground about three months after we began, we set the product itself, which was going to be a checking account for retirees.

CHAD: What were the factors that went into choosing the partner that you ultimately chose?

SAM: Beyond your standard enterprise vendor selection, we wanted to make sure that it was secure, and we wanted a specific set of features. In our space, there are about six different companies that provide what's called Banking as a Service technology. And so that was one of our key vendors is the technology company that works with the bank to allow us to open checking accounts, fund accounts. And most of those companies have been around for only a few years. And so their products themselves are hardening and being built.

And about $200 million I would say has been invested in those companies last year. And so we wanted one that was well-capitalized. We wanted one that had not had any IT security issues. We wanted the underlying bank to be aligned in our mission. Retirees have a variety of specific financial needs. A lot of our product development involves working very closely with the bank. And so, we needed to make sure that the bank itself that they worked with was on board.

And lastly, we talked to other customers, and that was ultimately the most valuable thing in our experience and not just the customers that they refer you to but the customers who have left for one reason or another. Those were the major factors that we chose in our Banking as a Service provider. And then, beyond that, that's one piece of the puzzle. In our bank tech stack, we're looking at around 15 different partners across all parts of banking. And that's the largest and most important one. And those were the criteria we used to select.

CHAD: I often say when I'm looking at building a product or service, and we look at those integration points with external vendors, it is one of the riskiest parts of building a product because you're not in control of it. So from a business perspective, it's risky. But also, from a technology perspective, that's where estimates can get out of whack.

And things can work not like you're expecting or like the documentation said or just surprises crop up along the way. Or when something goes down, your product is broken. And your entire product [laughs] basically is built on those vendor relationships. So, how do you minimize that risk and work in that environment to make a business that works and a product that works?

SAM: [chuckles] I suppose the answer is with a lot of prudence, thoughtfulness, and care at a high level.

CHAD: [laughs]

SAM: I was actually just talking with a CTO friend of mine just talking about how in a lot of startups, one of the skills that I most ask of engineers and engineering leaders early on is vendor selection and how I hadn't seen an interview process that really helped get at that. It's a core part of a lot of technologists' jobs and particularly a lot of engineering folks' jobs. The API docs looked good but did he test it or evaluate it? Was there a third-party tool you could have used instead of building in-house?

Those are the sort of questions that a lot of times early-stage startups are answering all the time. And I had yet to see an interview that got at that. So it's a really shrewd point and one that I hope that as technologists and particularly early-stage startups become more about really going deep in one area and then leveraging third parties elsewhere, I hope that we start actually hiring and developing criteria to do that with the people that we assemble.

I think the first part what I would say is we described a little bit about the risks. We went through a risk mitigation exercise, which smells very enterprise-y. It's kind of the sort of thing that you would expect exists in some massive waterfall with a Jira board mainframe computer but just listing like, here's this integration. If this were to happen, what would we do? If the API went down, what control do we have, or how could we minimize the impact on our customers?

That exercise across some of our biggest integrations helped us select and take on the risks we wanted and avoid the ones we couldn't. So there was a lot of conversation about the sorts of failures we could put up with and how we could put up with them, and the sorts of failures we couldn't. And then really testing for the ones we couldn't to make sure that we were making as good a choice as possible.

Despite that thoughtful answer, it was the best we could do. I would say that, particularly in a space that's as fast-moving as Banking as a Service, I would say that a lot of it is still that soft skill, that relational conversations with other teams and folks and whether you trust the team that you're trusting to execute and build what they said they're going to build and that hiring skill but also a good bit of luck as well.

CHAD: So correct me if I'm wrong, but up until Sagewell, where you're CEO, you had been CTO of the other companies that you founded and worked at. Is that right?

SAM: Yeah, that's correct.

CHAD: So, what has the change to being CEO instead of CTO been like for you personally? And was that choice clear from the beginning with Sagewell?

SAM: So far, it's been incredibly rewarding. I would say in between startups; I actually volunteered at an organization called PathCheck. And while my title was CTO, the scope of that included partnerships, vendor negotiations, CISO exercises, product. It was a pretty expansive CTO role. And I found myself really energized by the breadth and the ability to work with even more really talented, thoughtful experts in their own domain and empower them to do more. And so I knew in my next role, I wanted more of that breadth.

There's an essay that classifies folks as foxes who can do a little bit of everything or hedgehogs who can do one thing really well. And I'm a super fox. [laughter] I love doing lots of things. And so CEO to me is just like an opportunity to...it's maximizing breadth and maximizing difference of experience. And I transitioned, I'd say, from a normal CTO role to a beefy CTO role to making CEO a pretty natural step from there.

CHAD: And your co-founder is named Jeff Wright, and he's the COO. How did you meet him and get started with Sagewell?

SAM: Jeff and I, it's been wonderful. I was trying to figure out how I was going to get engaged in pandemic work in April of 2020 after leaving my last startup while it was being sold to Capital One. And I was talking with a founder friend of mine, a guy named Ty Harris, who is the CEO of an Insurtech company called Openly. And he was previously the CTO at Liberty Mutual. And Ty and I had a couple of lunches and conversations, and I was talking to him about how it is getting involved in COVID stuff and how I was ultimately my species as an entrepreneur, and I was going to be building something again.

And he connected me with Jeff, and Jeff and I touched base quickly in April. And it was a little bit like a frog in the pot sort of situation where it started like, yeah, maybe we could build a company. Let's riff on some ideas and see what's out there. And it was a really, really natural progression from August to a couple of evenings, maybe a Saturday call or two, to most evenings and definitely a Saturday to oh, man, when should we transition?

CHAD: You were both working full time on other things at the time. You were working with PathCheck.

SAM: Yep, exactly. And so he was the CPO at a company called Plymouth Rock, and I was working at PathCheck. And not to go into PathCheck's story too much, but PathCheck was largely deploying a research technology, the Google and Apple Exposure Notification protocol. And it became clear that most of the states that were going to do anything were already going to do it. And so, it was natural to start thinking about what was next in August and September. And so, as my species does, that then became the night and weekend project to figure out what's next.

CHAD: So you mentioned that this is a space that is typically not strongly funded. So was that a challenge for you as you were getting started? How did you get that initial, you know, where did your initial funding come from? And I know you recently raised, at least it was announced, 5.3 million in January. So what was the transition from those early days? Where did the funding come from to ultimately getting the investment in this last round?

SAM: Jeff and I worked in the fall of 2020, met our CTO, Chris Toomey, in November actually from connection through a friend. Early on, we were a team with a demo. We really knew that we cared about seniors, and our background is in financial services. We were trying to think of a new product for seniors and so a financial product for seniors. And so, around January, we sharpened our pencils on the user research side of things and the product side of things. And once we had a clearer sense of the product direction we wanted to take, ultimately building banking for retirees, we began the fundraising process.

CHAD: So were you essentially self-funding at that point?

SAM: Yep. So we were self-funding from January-ish till May. I find that skin in the game to be… I wish I was the sort of founder who could think about flawless ideas without a little pressure. But in my experience, it's actually been where unless I jump in, unless I can have a little bit of pressure, my ideas aren't often as refined as I'd like. And so Jeff joined it full-time in February. And then we fundraised through April, closing a 1 million pre-seed, which is pretty common in fintech.

Most financial technology companies the banks won't talk to you until you have at least a million dollars in funding. And so we raised the money we needed from...and who did the money come from? It came from Point Judith Capital, who actually had invested in Ty, the guy who connected us, with his company Openly. So we had our initial conversation with David, who's been absolutely wonderful at Point Judith Capital.

And also, Jeff and I knew that innovating for a vulnerable population, ultimately retirees, meant that we wanted to have folks from the beginning who represented the seniority and seriousness with which we are taking our work. And so the second investor who in between the two of them took most of that million was Crossbeam and Raj Date at Crossbeam, who's the former Deputy Director of the U.S. Consumer Protection Bureau. We really wanted folks around the table who knew what innovation looked like and fintech innovation like David, as well as folks who understood the world of government and finance like someone like Raj to innovate thoughtfully with this demo.

CHAD: Was it difficult to get those funding rounds?

SAM: The first one? Yeah, the first one was about two months. I thought it would have taken about a month. The second one the market is pretty crazy right now. And I would say between my first company and my second, it used to be that you'd set aside six months to fundraise, and so I'd prepared for a six-month fundraise. Started kind of in early October two weeks in, and they were like, "Wow, you've already been in the market for two weeks?" [laughter]

And I was like, what? I was totally off base in terms of what was the new normal. Ultimately, that round came together in about a month and a half as well. And so we had a lot of interest. The second round that 5.3 million went from not a ton of interest to tons of interest and lots of folks around the table and having to push folks out or turn folks down pretty quickly. The first round, I would say for a pre-seed, one to two months given that the idea was hardening, sounds about right.

The second one was about one to two months but was a little...a lot of people would get excited by the market; they'd get excited by the team. And then they'd say, "You can't get a senior to open up a bank account," and then they'd come back. And then we found one believer alongside David and Raj, who had been with us. And once we got the folks at 25Madison and Merrill, especially, the rest of the round came together really quickly.

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CHAD: Given that you were able to put together a round quickly, how do you decide ultimately not to take even more money? What are the factors that go into deciding how much you're trying to fundraise and how big the round is going to be? And is there pressure as you're doing that to maybe go even bigger?

SAM: Yeah, we had, I would say maybe seven and a half million dollars interested. And ever since we've closed, we've had multiple firms who are interested in a new round of capital. The market is really, really quite founder-friendly right now. I think ultimately, for any founder, what you're trying to do is create as much value with as little capital as possible. That's ultimately the game that you're trying to play now.

For a little baby company, it's often really hard to figure out how much money or how much value you'll be able to create over what amount of time. There's so much to figure out. There are so many bets and learnings and risks that it's often very hard for a company to say, with $5 million, I'll create $20 million in value. So ultimately, if you're a founder, you're incented to give away as little of the company as possible and create as much value from that.

And so when we were doing our modeling, we actually thought that it was somewhere closer to four of what we needed to create the amount of value needed to raise our A. And we ultimately bumped it up to 5.3. And there's a good bit of advice you hear a lot among founders that raising a bit more than you think is prudent, and anyone who has managed a budget knows how that can go. So we ultimately did go up to 5.3.

But taking more would have meant that we were paying a premium where we could get that million dollars maybe in a year's time, and we'd be giving away a quarter-point or a half a point of the company for that million where we might be giving away 1% or 1.5% of the company now. So it's all about creating as much value with as little money as possible. And it's easy to get lost in the big rounds and the big numbers. But ultimately, it's pretty simple math.

CHAD: And correct me if I'm wrong, and this is a question as much as a statement. So to reiterate, the rounds you're talking about are seed rounds. And so traditionally, what that means is that the majority of work that you have to do is just making the product. But in the space you're in, there is a point in time where you've made the product, and you've shown the traction, so what you have becomes more valuable.

And so it might be that the next round, which is maybe a Series A, a significant portion of that capital would be spent on something else like marketing or sales teams and that kind of thing. And you're growing beyond just the product development at that point. Is that how you're thinking about this, or am I wrong?

SAM: So it's funny that it's really changed the names. The round size what they mean has changed more in the last two years than ever before, and I would say that, particularly in fintech, because fintech has a number of unique challenges. So I would say that that $1 million round that we raised in May that was really about building a very basic product, a very truly minimally viable acceptable product.

And then the seed round in fintechs is often about getting to product-market fit or just demonstrating you can reach your end consumer or target user. In fintech, it's often not quite as much tied to a certain amount of revenue at that stage. It's often about just demonstrating that you can get to that user, and that's because, in financial technology, the cost to acquire is often quite high.

And so for a company that only has raised, say, a $5 million pre-seed because of the gravity, because it often costs hundreds sometimes thousands of dollars depending upon the market to acquire a specific user, the math is such that you're just not going to have that many users, and you're not going to be able to get to a certain amount revenue. And so often in fintechs, 1 million gets you...that pre-seed gets you that initial product. The seed is about demonstrating that you can scalably get to that end user.

And then the series A is really about blowing that out and starting to exploit that marketing and acquisition machine that you've been building to start creating revenue. That's a little bit industry-specific. Other industries will have similar or different terms. And depending upon what sort of branding a firm might want for the round, you also might hear $100 million pre-seed. You hear those things as well. It's a crazy time to be building a company.

CHAD: So you mentioned Chris Toomey, who's the CTO of Sagewell, and he was previously at thoughtbot. As a prior CTO, what were some of the things you looked at in terms of finding Chris and deciding he was the right one to join your team as CTO? I imagine your standards were pretty high.

SAM: Yeah, and Chris met them quite happily. As a CTO transitioning to CEO, I think you have to understand your strengths and weaknesses as a CTO as well as the learning curve that you might have stepping into your new role as a CEO. And I would say that one of the fortunate things is that Jeff, my co-founder and COO, we actually have a pretty unique set of skills that can span a lot of different domains.

And so I would say that looking at Jeff, Chris, and myself, we really had to make sure we had our bases covered to build the financial and technology product we needed. I would encourage folks building a company early on to really think about your strengths and weaknesses, your founding team's strengths and weaknesses.

And as I was getting to know Chris, kind of the initial handshake agreement starting to build and prototype various solutions, I think that I was particularly impressed and looking for someone who was willing to have a deeply experimental and MVP mindset while managing the risks of working with a vulnerable population. And so over the course of December through March or April, in dealing with and spinning up a couple of different prototypes with radically different product strategies and end products, I was able to see how Chris was able to be mature and shrewd about where he could cut corners, where he couldn't cut corners and then execute accordingly.

It's funny, Chris and I were talking at our one on one a week or two ago. As a CTO, I know a little more of what's possible. I know if I come in and say, "I want the Taj Mahal," I know you'll get walked back down. Chris and I over the past year...I often come to Chris, having already teared down my Taj Mahal. And I'm like, "Well, Chris, what I really need is one little specific problem." And Chris and I actually set a goal between us that I actually kind of come to him asking for the Taj Mahal next time [laughter] or not next time but sometime in the next year.

Because I think one of the things I've had to check or do in CEO is let Chris do CTO's job and not internalize all the time his voice and concerns but actually put forth a vision and not be afraid about the fact that it isn't something that we can get to market in a week or that we can't ship in three or four weeks’ time, which is an interesting contract that I think we've developed and an interesting growth area. And it's my job to throw out bigger ideas, not to be the one who tears them down all the time, which is fun, and I enjoy doing that with Chris.

CHAD: Yeah, that's an interesting perspective. And I often even working with clients and consulting want that because if you're only getting the small pieces all the time, you cannot be privy to the big picture of what we're aiming for. And that will often lead you to maybe not taking everything into account, either that's on the roadmap or down the road. Or realizing, oh, you're disappointed now, but that's because I didn't know that you wanted to do this. If I had known, then we could have done this in a different way or something like that. And so, getting a sense of that big picture is often important.

SAM: Yeah. And it's a fun, I'd say...yeah, and growing with Chris and figuring out that he's the right person for the role as a CTO turned CEO means kicking off the ladder and actually just stepping into my role and letting him do his, which has been a fun contract to establish.

CHAD: So, did you work with Chris as a contractor before committing to him as CTO?

SAM: Yeah, we were in a consulting relationship. I think Chris was politely under billing. And the pretext is always that this was something that we were really aiming to build a company together, assuming everything worked out across Chris, Jeff, and I. And so, he did start in that capacity. And then I'm trying to remember the exact timelines. Sometimes the paperwork is well after the actual agreement whenever you're creating these companies. But in a few months’ time, definitely by July and probably by May, we were building the company and off to the races.

CHAD: Now, is that a path that you would recommend to other founding teams looking for a CTO is to not commit early to really make sure that you work well with someone, maybe through a contracting relationship first?

SAM: Yeah, I think ultimately, if you're going to be going on a journey, a decade long journey, a lifetime-long journey, through highs and lows, I think the best way for everyone to know what they're getting themselves into, the excitement, and the reward, and the aches, and the pains and the sleepy [inaudible 33:31] in the morning is by working together, and I don't think there's a shortcut. In this case, it depends a lot on the situation. It depends if folks are in a position where they cannot take pay. It depends on whether nights and weekends are free or they have flexibility in their other roles.

But generally speaking, I think that ultimately, you're trusting, and your founding team is going to be taking so many risks together that you want to go in as eyes wide open as possible and have removed as much founding team risk, disagreements, misaligned working styles, misaligned visions, or preferences as possible. My coach used to say that that's the number one reason why companies at the seed stage fail is management teams and founding teams.

And so as you're thinking about building your company, and I can't emphasize this enough, mitigating and removing founding team risk, however possible, with consulting being one of them and navigating a tough conversation or two being another, is absolutely core to removing as much risk as possible for your startup.

CHAD: That's great advice. And just like you and Jeff had a time of working together before you actually started a company together, I think it's great advice to try to find ways to do that with other early members of the team too because it's a big commitment, and you want to make sure that you get it right.

SAM: Exactly.

CHAD: Well, you've reached sort of the pinnacle of having now someone on your team that used to work at thoughtbot. I think I'd be remiss if I didn't point out that we have another podcast at thoughtbot; it's called The Bike Shed. And Chris started as a host on that show while he was on thoughtbot, and he continues that to this day along with Steph Viccari, who's a team lead at thoughtbot.

And so if people are interested in hearing about Chris' work now at Sagewell and following along with the team and the work that he's doing there as well as the work we do at thoughtbot, people can check that out at bikeshed.fm. Sagewell is not a client of thoughtbot. But you've worked with thoughtbot before as a client twice, right?

SAM: Yeah, exactly, both at my first company Freebird, which was sold to Capital One, and at PathCheck, the non-profit I worked at.

CHAD: So you specifically, I assume, then made an effort to recruit from thoughtbot when you started Sagewell. [laughs]

SAM: I would say I know and love the way that thoughtbot approaches building software. And I know and love the people that I've worked with from thoughtbot. And I would say that it was as much a feature of being in the same communities as it was specifying a specific group. But you guys have created a great culture. [laughs]

CHAD: I'm just kidding. I didn't actually think that that was the case, but I can guess a lot of the benefits of working with someone who's worked at thoughtbot before because of the level of experience and the level of skill and communication and everything that people at thoughtbot have. But I'm curious, what if I turn that around? Is there a downside to hiring someone who worked at thoughtbot previously to your team?

SAM: So one of the things that I love about, particularly early on, we have a hire that we just made recently. She worked at a senior living facility for four or five years and then worked at Wells Fargo for four or five years. And before, we had a bunch of fears, and this new employee listed five or six totally different fears than we ever would have thought of. And so now we have way more fears. And part of that can be unnerving, and part of that can be challenging.

And I would say that one of the challenges of working with a team that builds software in such a clear culture is that you might not get all the fears. You might not get certain sorts of diverse perspectives or headaches because of a particular way that product and engineering are conceived. And so one risk...it’s kind of the unknown-unknown sort of situation, but it's real in startups which is I think that making sure you have diverse perspectives across the domains where you need to be deeply an expert for folks who are very similar to you is a major risk.

CHAD: That's great. Well, Sam, thanks for stopping by and sharing with us. I really wish you and Sagewell and the entire team all the best.

SAM: Awesome. It was wonderful talking.

CHAD: And if folks want to find out more about Sagewell Financial or follow along with you or get in touch with you, where are all the best places for them to do that?

SAM: sagewellfinancial.com is our email. And if you or your parents are interested in what we're building as a customer or a member, you can sign up there. If you'd like to reach me, I'm mostly on Twitter following cute animals and occasionally a good tech post @Ferrum_of_omega. And if you'd like to contact our company, you can just go to /press and fill out the form there.

CHAD: Awesome. And you can subscribe to the show and find notes for this episode along with a transcript of this episode and all past episodes of this season at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. And you can find me on Twitter @cpytel.

This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks for listening and see you next time.

ANNOUNCER: This podcast was brought to you by thoughtbot. thoughtbot is your expert design and development partner. Let's make your product and team a success.

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