Founder Calls: Ismail of Hingeto

One of the most valuable things for me as a startup founder is having coffee, breakfast, walks around the neighborhood, etc with other founders. Startups are hard, and founders supporting each other makes a big difference. I thought it might be nice to make some of that “mutually supportive founder conversations” experience a little more accessible. Plus, I really enjoy talking to people building new things and companies.

Akintunde Ismail Maiyegun is a co-founder of Hingeto, a startup at the forefront of a new category: Commerce as a Service.

When I first heard about what Hingeto is doing, the company struck me as one of those “why hasn’t this existed before” stories. Hingeto solves complex inventory and logistics problems for fashion brands. If you’ve ever planned, sold, and shipped a physical product, you know about these headaches. I wanted to talk to Ismail about the genesis of Hingeto, how the company has evolved, and his deep experience as a startup founder and engineer.

“He thought to himself: how can he use data to predict things that customers want?”

Hingeto grew out of years of professional experience in retail fashion. Ismail’s co-founders Leandrew Robinson and Yaw Owusu-Barimah spent years at, a major online commerce company. They saw patterns in how successful companies solved practical problems around demand prediction, financing, manufacturing, and distribution. Those problems have nothing to do with the artistic side of fashion, but they are make-or-break challenges for all fashion companies.

My co-founders Leandrew and Yaw both came from what was at the time the largest online streetwear retailer.
Leandrew founded a division within the company called PLNDR, which they grew to being a $40 million business in five years, and so just in their day to day, in dealing with those brands and then seeing which brands were successful and which ones weren’t successful, and seeing which ones would go out of business, they were able to hone in on some of the problems that they saw.
Some of them were very avoidable and they started to notice the shift — that everybody kinda sees right now — with retail in general being just a lot more difficult. And so, he thought to himself, how can we use data to predict or more smartly produce things that customers want? Instead of, you know, a room full of artistic people thinking that they can dictate what consumers want, when that’s just not the case.”

I find Hingeto interesting on a lot of levels, but I’m particularly fascinated with companies that aim to transform huge, invisible parts of our economy. Consumer-facing startups like Facebook and Google get most of the attention in the tech world, but the majority of successful startups are actually enterprise-facing, business-to-business companies. These companies are often built around their founders’ deep domain expertise; they are mechanisms for turning a few peoples’ experience and insight into large-scale improvements for an entire industry!

“At the core, they all fundamentally suffer from the same things”

Figuring out who you’re selling to is as important as figuring out what you’re selling. (In fact, the who and the what impact each other so much that they aren’t really separate questions.)

Enterprise startups usually focus quite narrowly, early on. Selling a tech product to a Fortune 500 company is not the same as selling a product to a small business. The sales process, pricing, and how the product is deployed and supported are likely to be completely different.

​​Ismail and his co-founders made the somewhat unusual choice to build their platform so that they can serve very large mainstream retailers, boutique brands, and everyone in between. I asked him about the difficulties of selling to partners at different scales.

Ismail: The funny thing is, at the core, they all fundamentally suffer from some of the same things, so it’s not that difficult … when you know how to talk to the challenges they face.
It’s the exact same problem, just positioned slightly differently. So, surprisingly, the pedigree that’s in the founding team and in our company in general, has worked, when it comes to selling to both. We’re able to talk to the biggest of the retailers and the smallest of the brands, and the most influential of them, because again, we can speak to them, and they respect our teams background — oh yeah, these guys get us and they understand what we’re facing.
So actually oddly enough, yes it’s been difficult for some, but it’s just because of the nature of lots of cooks in the kitchen and lots of tiers that you have to break through in bigger organizations.
Kwin: I have to say, I really do think it’s super impressive. One of the things that we were worried about when we started our company was being really clear about market segmentation, because we knew if you get pulled up-market or get pulled down-market accidentally, that’s going to kill your company. And that’s a mistake a lot of companies make is that you go to market with a particular target customer, and then you get stretched.
Ismail: Yeah, we are cognizant of that possibility, and we think about this all the time for sure… this customer and this customer are alike, [but] there may come a time where yes we’re one company, but we have these two very separate teams working on these two very separate types of customers. Or we may end up saying, hey look, we’ve tried both, this is the customer that makes the most sense for us long term.

“A lot of people think they’re hustling, but they’re not really hustling”

Leandrew and Yaw bring deep knowledge of the retail fashion industry to Hingeto, while Ismail brings extensive experience with engineering implementation, engineering management, and technology strategy.

For many business-oriented founders, finding a technical co-founder is a frustrating quest. I get dozens of e-mails a year asking me how to recruit someone like Ismail, so I asked him what convinced him to partner with Leandrew and Yaw.

There are many forms of hustles that exist and a lot of people think they’re hustling but they’re not really hustling.
Certain people exhibit those [positive founder] traits — not just slick salesmen-type stuff — but just pure hustle, willing to do whatever it takes to close a deal.
To think critically through things, and to inspire, and to get me to buy into a future, to buy into the vision — these are all things that can be learned, in my opinion — though some people just naturally have them. But some of these things can be learned and coached and improved upon over time.
So that’s what I would tell people: just work your butt off on those things. And obviously the more capital you can secure … it’s a very different conversation when you come to me and you say, “hey, I have my uncle, my aunt, my mom, they’re all committed to giving me $30 K or $5 K or $2 K each, but I need to get to this milestone.”

“Even if you were presented with a playbook, there’s going to be a curveball thrown at you”

A technical co-founder’s role isn’t just writing code, though that can certainly be a lot of the initial workload. As a company grows and the team inevitably expands, every founder has to branch out into team management.

Managing people is a skill set and a learning curve of its own. Ismail is an engineer’s engineer, and he’s been managing teams for many years. I was curious how he defines his role and allocates his time at HingeTo.

In particular, I think a common challenge for a technical founder at an early-stage company is figuring out how to balance being simultaneously an engineer writing code, and a manager worrying about people and processes.

Ismail: I also struggle [with this]. There are some times where the amount of time it will take me to explain this new request, I might as well have just done it. But I need to not do that … because I know what I’m doing is I’m educating and empowering the engineer to be able to put the pieces together for a much greater ask down the line.
There’s just no playbook [for management]. Humans and personalities are so different, and even if you were presented with a playbook, there’s going to be a curve ball thrown at you and you’re going to have to learn how to deal with that, and that only happens by learning and experiencing it.
And you can’t forecast it happening, you just deal with it.
Kwin: Because it’s people. People …
Ismail: Yeah, people. People are, people are awesome!

I have an enormous amount of respect for good managers — the kind of respect you only develop from learning how hard something is through direct experience!

I find myself returning over and over to two blog posts by Marc Hedlund. “What do you make as a manager?” talks about the importance of focusing on the job of management, and the rewards of doing so. Management in ten tweets distills a career’s worth of specific, succinct, empathetic advice.

“They believe we’re the team to do this”

Many aspiring startup founders are surprised to discover just how important personal relationships are to fundraising. The vast majority of seed-stage tech investments happen through personal relationships. This was the case for Hingeto. Co-founder Leandrew Robinson was a known quantity to legendary tech investors Freada Kapor Klein and Mitch Kapor.

But even with a strong investor committed to leading a seed round, if you’re trying to raise a substantial amount of money for an early-stage company, you still have to convince other investors to get on board!

I asked Ismail about Hingeto’s funding story. It turns out to be a great example of working early on with a single lead investor to build towards a funding round, and an example, too, of how powerful Y Combinator is as validation for an early stage startup.

Again, much credit to Leandrew from his non-profit days. He actually interfaced a lot with the Kapor family.
And so it’s through that non-profit relationship that they are like, “man, this guy is a really enterprising dude — yeah, it’s in a non-profit space but there’s something about the way he goes about running this non-profit, and how he’s able to inspire these kids,” so they kept in touch. And when he actually got a job and rose up at his previous employer, they were like, “yeah, we were right, and, you know what, if you ever decide to do the for-profit thing, we’ll be your first money in.”
Interestingly enough, we still had a hard time raising money, because then the question became: “wait, why’s Mitch Kapor, you know, founder of Lotus 1–2–3, early investor in Uber, and all these other things, why’s he investing in a fashion or apparel company?” That seems weird. That’s outside of his area.
Seriously. And so it was just interesting. We actually had a very hard time raising outside of that [from institutional investors] … but [Mitch]was able to help us attract some other investors pre-product. We launched the product, started to get some traction … and a partner at Kapor introduced us to Michael Seibel.
I think you heard this story in the podcast. Michael Seibel’s like, “well, deadline’s passed, but you know what, sure … apply,” but we have to send it in by today. And so, we do it, we thankfully get in, but then YC tells us that uh, yeah, don’t raise anymore money.
And obviously we’re ecstatic, but we know how difficult it’s been to raise money.
But, I’ll tell you, the moment we whispered to some people here and there that “hey, we got into YC” we closed the amount in 24 hours [that we had been trying to raise] on AngelList. We felt like we knew what was best for us … we’d be foolish not to close out the syndicate that we already started anyways, and leverage the momentum we already had.
So we used that momentum … went through YC … grew 90% month-over-month for the three-month program. And, thankfully, we came out at demo day with somebody wanting to lead an extended seed round.
Kwin: I think a lot of the YC advice before the partners know you is going to be geared towards first-time founders, because that makes sense historically. Most YC founders are first-time founders. And it’s almost always the case that the first-time founders are going to get much more out of the fundraising process at the end of YC rather than at the beginning. But if you’ve done it before, all you need is that forcing function.
Ismail: Exactly.
Kwin: Everybody, when you’re raising money, is trying to create that forcing function. And it’s so funny that it wasn’t just a no-brainer to get people to follow in behind Mitch Kapor, who has this incredible, incredible reputation. But basically, those people didn’t see a forcing function.
Ismail: Yeah they didn’t see a forcing function, exactly. So, we saw it, and then, to that point, we kind of created it.
When we look at our investors, a lot of them have known us for a while or known of us for a while … they want to see us succeed for some reason, or they believe we’re the team to do this.

Fundraising for a startup is much harder than it seems like it should be, if you just read the tech press coverage of the startup ecosystem. Almost everyone finds this out the hard way the first time they try to raise money from institutional investors. Geoff Ralston’s Guide To Seed Fundraising is an excellent primer.

When people ask me for advice about fundraising, I always start out saying that two things are worth understanding right up front. First, most seed investments are made because of personal relationships and connections. Second, no matter how much people like you or how highly they think of you, most of them will need some kind of forcing function to actually get to the point where they write you a check!

“You see life through a different lens”

I asked Ismail about his experience in Silicon Valley over the past fifteen years, and whether he thinks the Valley’s much-documented issues with diversity are changing. Ismail and his two co-founders are black, and he talked a little bit about the competitive advantage of having fewer blind spots about potential markets.

Kwin: Hopefully that element of the Valley is changing, but it’s changing slowly.
Ismail: It’s changing slowly. I will say this: I think change is happening for sure. We had a lot of other VCs very, very, very interested, but pull out at the very last minute. Who knows why. Maybe that’s just their play book, if you will — pretend to be interested and then pull out at the last minute, who knows.
But … we got in the room. Now, of course, we were YC-backed. I went to Stanford. So I can only imagine what it’s like for people who don’t have that. Man, the orders of magnitude of difficulty, I can’t even begin to …
Kwin: Stanford makes a difference in the Valley, that calling card makes a big difference.
Ismail: For sure. For sure. So, yeah, I have faith that something is changing. I feel like entrepreneurship and money, because money has no color … whether people want to be or not, they’re recognizing, “my pattern matching is actually costing me money.” And there’s these other business ideas that may not sound like a huge, huge deal because you can’t empathize with it because you have a very different, I don’t want to say upbringing, you just see life through a different lens. And one example company that comes to mind is a company founded by my buddy Diishan Imira, called Mayven. Are you familiar with them?
Kwin: Only a little bit. Not as much as I should be.
Ismail: They sell women’s hair extensions. Which, if you know anything about …
Kwin: That’s a big market.
Ismail: A huge market, huge market, huge huge huge market. But the only people [in Silicon Valley] who took them seriously were people who either just happen to have a lot of black friends, or have a lot of insight into that market. Their lead investor happens to have a black wife. So, it’s just like, yeah, yeah, it’s just funny.

Here’s the full video. A few more highlights:

  • Hingeto started life as “Kickstarter for fashion” (03:20)
  • The Hingeto tech stack (31:45)
  • More discussion of trying to recruit or being recruited to be a technical co-founder (14:20)
  • More about fundraising, pitching investors, and — from the other side of the table — identifying startups that can be billion dollar companies. Michael Seibel was almost alone among investors in betting on Airbnb very early! (52:22)

I hope you’ve enjoyed reading/listening to Ismail as much as I always enjoy talking to him!