Why it matters:

  • According to lessons learned from companies in expansion mode, startups eyeing growth would be wise to hire generalists versus specialists in the early stage of a business venture.
  • After determining what product or service you’ll provide, identify your audience — both what they want and how to reach them.
  • When negotiating with a potential business partner, unpack the concrete needs behind their requests so that both parties’ interests are served.

Startups Alleyoop, Culprit Underwear and Doorkee have learned a thing or two about growing a business.

Direct-to-consumer beauty brand Alleyoop has landed access to a national consumer audience via HSN, where it’s pitching products designed for busy women to the platform’s 92 million home viewers.

Culprit Underwear has grown from selling 20 pairs of underwear in March 2020 to 20,000 pairs by January 2021, largely via word of mouth.

And real estate player Doorkee grew from a base of 300 rental units in December 2019 to onboarding over 13,000 units by the end of 2020 by connecting apartment seekers to departing tenants.

While the beauty, fashion and real estate companies reflect disparate business sectors, their trade secrets on what startups must know to grow transcend industries.

Here, the founders of Alleyoop, Culprit and Doorkee offer their takes on key tools in a startup’s growth kit — from hiring “generalists” and tapping the “cultural zeitgeist” to leveraging a little-known-yet-highly-effective negotiating strategy.

 Alleyoop CEO and founder, Leila Keshani, sitting on a couch surrounded by bags of her products.
Leila Keshani, CEO and founder of Alleyoop. — Alleyoop

Alleyoop: Hire ‘jacks-of-all-trades’ first, and save the specialists for later

CEO and founder, Leila Keshani:

The best advice I could give is to make your first few hires jacks-of-all-trades. Start with people who can do a little bit of everything and do it all well. Then, as you grow, you can start to intentionally hire specialists with very defined skill sets. As a startup, you have to test a lot of different things to see what’s going to work, so you have to be flexible and be willing to try a lot of different things. I experienced this firsthand. At the start of our company, we hired a couple of specialists and quickly realized they were struggling to adapt to the changing needs of the company as we continued to pivot our strategy.

 Product image of Alleyoop's "11th hour" eyeshadow stick.
Alleyoop's founder Leila Keshani credits her success to beginning flexibly, and then focusing on the strategies that work in order to scale. — Alleyoop

It’s important to have generalists early on in your company who have broader skill sets and thrive in fast-paced, changing environments. Then, once you’ve nailed a strategy that’s working for the company, you hire someone who specializes in that area to help you scale it.

Once we tested a lot of different things, we learned what was working for our brand specifically and where we wanted to contribute more efforts. Those areas included email marketing, influencers and content, so we decided to hire specialists to help us scale those departments. These roles included a senior CRM manager, an associate brand ambassador and a content strategist. Following these hires, we were able to hone in on our email strategy and cadences, create a scalable influencer marketing program and start producing more meaningful content across all platforms.

[More here on tapping top influencers by industry.]

 David Dinetz (left) and Dylan Trussel, co-founders of Culprit Underwear, posing in suits.
David Dinetz (left) and Dylan Trussel, co-founders of Culprit Underwear. — Culprit Underwear

Culprit Underwear: Carve a differentiated niche that resonates with a consumer ‘tribe’

Dylan Trussell, co-founder:

The key to successful growth for a startup is identifying a hole in the market and filling it with the best product or service possible, regardless of name or branding. Co-founder David Dinetz and I are both filmmakers — we never envisioned we’d be in the underwear business. After establishing our creative agency and producing content for global brands like Virgin and Mercedes-Benz, we realized we wanted an outlet for our subversive content, but with full autonomy over the product.

We thought about the various products we use every day and where they were lacking, and underwear stuck out as having the most room for improvement. We asked ourselves, ‘If you could imagine the perfect pair of underwear, what would it look like?’ It had to be made sustainably in the U.S.; insane comfort was a must; it needed to be supportive enough for the gym but sexy enough for a date; and it had to have a sense of humor. We couldn’t find anything like this on the market, so we created Culprit Underwear out of a desire to make the best product possible for both men and women, and it’s what’s kept our current customers coming back for more.

 An upside-down shot of a model playing basketball wearing Culprit Underwear.
The Culprit Underwear co-founders emphasize how identifying and filling a need in the market, and then identifying and understanding their target audience led to their success. — Culprit Underwear

David Dinetz, co-founder:

Once you know what product or service you’re going to provide, you need to know your audience — both what they want and how to reach them — and how to capitalize on the cultural zeitgeist. Since Culprit was born out of a desire to create shocking and hilarious content, we knew our recipe for success would be to meet our customers where they are with that content. We found our tribe early on with hilarious short videos like, ‘It’s Time to Torch Your Underwear,’ which has been viewed almost two million times on YouTube, and The Pig Short, a print which we designed in response to the GameStop saga. All of the proceeds go to GameStop stock, and customers will be able to decide when to sell and what to do with the gains.

Making this content has allowed us to not only hop on the news cycle, but reach new customers, making us one of the fastest growing underwear brands out there.

 Headshot of John Fagan, founder of Doorkee.
John Fagan, co-founder of Doorkee. — Doorkee

Doorkee: Expert negotiators get to the crux of ‘what matters to the other side’

John Fagan, co-founder and CEO

In my law school negotiation classes, we’d often refer back to a short but powerful book called ‘Getting to Yes,’ which outlined six key negotiation strategies that can help both sides get more of what they want.

In business, especially in startups, you don't usually have the upper hand where you can just force your way into the deal you want — so you need to get creative. Instead of arguing over how to split 10 oranges and who gets more, you can realize that you only want the oranges for the juice while the other side is just looking for the peels. If you can understand the ‘interest behind the position,’ you’ll often get to an agreement that addresses each side’s concerns and meets their needs. [In other words,] when you understand the actual needs behind the request, you start to come up with creative solutions.

 Image of the steps involved in working with Doorkee: Give Notice, Register Apartment, and Get Refund.
Doorkee co-founder John Fagan emphasizes understanding the needs of the other party during negotiations, because that helps to best determine your own strategy. — Doorkee

At Doorkee, our primary focus is creating a peer-to-peer apartment rental marketplace where apartment seekers can find their next apartment ahead of time via the departing tenant, who earns $1,000 when the future tenant signs their lease. Our landlord clients often begin by saying, ‘I don’t want you contacting our tenants directly.’ At first, we tried bargaining them down on the number of reach-outs, or the method. That got us nowhere. But once we sought to understand their interest behind this position, it was clear that landlords were afraid we were going to encourage their tenants to move out.

Once we learned their real concerns, we were able to share our reach-out strategy and content, and confirm via our historical data that Doorkee doesn’t increase the likelihood of a tenant leaving, just the likelihood they give early notice and cooperate in getting the apartment rented before vacancy. We assuaged their fears, and now they’re saving a ton of time and money on vacancy, their tenants are happier and Doorkee is growing faster than ever. Win-win-win.

Novice negotiators want to grab a larger slice of pie. But experts know that by truly understanding the position behind the interest, you can expand the pie so everyone gets more of what they want. It's an advanced move because it's unintuitive — neophytes just think about what matters to them and what the other side says they want. True negotiators find what matters to the other side, so they find a way to provide them that without giving up too much of what they themselves really want.

[Read here on why innovation should be built into business models.]

CO— aims to bring you inspiration from leading respected experts. However, before making any business decision, you should consult a professional who can advise you based on your individual situation.

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CO— is committed to helping you start, run and grow your small business. Learn more about the benefits of small business membership in the U.S. Chamber of Commerce.

Published March 29, 2021