Are Thoughtful Gifts the Secret to Hot Leads, Employee Retention, and More? This 8-Fig Founder Bets on It

When Millie Tadewaldt worked in a corporate role, she wondered why buying company swag as employee gifts was so disconnected from how modern people shop.

“The people who bought branded merch at most enterprises were usually women in their 20s and 30s in positions like HR or marketing,” she says. “But when I was trying to buy company swag, this gentleman in a suit rolled up with a suitcase filled with sweatshirts. He wouldn’t let me try them on or keep any. He was a lovely guy, but the buying experience just hadn’t kept up with the rest of ecommerce.”

This peek into corporate gifting and her previous experience working with early-stage startups inspired Millie to create a corporate gifting startup, Brilliant. Her goal was to deliver the best corporate gift experiences in the world for both senders and recipients.

More than just a good gifter, Millie’s also a former design major, a graduate of Harvard Law, a self-taught software engineer, and a previous investment manager at AngelList. Her journey through America’s burgeoning tech scene in the mid-to-late 2000s brought her face-to-face with the challenges of most early-stage startups. She also saw how pursuing venture capital could dilute founders’ visions.

After half a decade of working in the startup industry, Millie saw businesses repeatedly making the same mistakes in their relentless pursuit of funding. She also noticed corporate gifting had failed to arrive in the twenty-first century, with most lacking an online portal for purchases and fulfillment.

In 2015, she synthesized her learnings into a tech-enabled gifting business and grew it for nine months as a solo operation. She stored everything in her garage until she bought a warehouse to meet her exacting packing standards. As of 2022, her business has 93 full-time employees and completed gift campaigns for massive startups like ZipRecruiter and Airbnb.

Here’s how Millie broke startup conventions and navigated hiring for complex roles on the road to creating her eight-figure gifting business.

How to Love Hard Work

Millie believes her enviable career trajectory is due to her love of type-two fun, a term coined in 1985 by a geology professor at the University of Alaska, Rainer Newberry. “Type-two fun is the stuff that’s painful while you do it and fun after you’re done,” she says. “But I enjoy type two-fun even during the painful part, which is probably why I like coding.”

That love of type-two fun spurred Millie to teach herself software engineering as a teenager growing up in small-town America. After graduating with a degree in design from UC Davis in 2003, she used her skills to build a software engineering firm with a proprietary CMS. She’d help clients build websites and teach them about how databases could change their lives. Eventually, she became bored with building the same website again and again and decided to give Harvard Law a shot.

“I wasn’t sure law was for me even before going to Harvard, but I figured, ‘Hey, it’s Harvard, why not.’ Pretty quickly after I got there, I felt convinced that I didn’t want to practice law given the lack of agency lawyers typically have over business decisions.” 

Instead of going into law (though she passed the California bar), Millie spent the next two years as a consultant for The Boston Consulting Group. Then, in 2010, she became the managing director at a business called Sandbox Industries in Chicago in charge of their in-house web-based startup foundry. In her role, Millie helped create and incubate startups as they scaled and looked for funding. She credits the experience for teaching her the bootstrapping mindset.

“I was motivated and well incentivized to work hard because I, the founder, and whoever I recruited to work on each concept with me would own a small portion of each startup. We operated on a shoestring budget and we needed to demonstrate results without much R&D, so we focused on ecommerce. We always attempted to get them Series A funding. However, because Sandbox Industries took a majority stake, VCs were usually skeptical.”

Millie became particularly disgruntled with VCs after a poor experience pitching for a mail-order styling company she was growing called CakeStyle.

“We were raising at the same time Stitch Fix was raising its Series A,” Millie recalls. “My company was a higher-end version of Stitch Fix. We couldn’t raise money despite doing $500,000 a month in revenue. It was difficult to defend because they’d ask why this other entity owns 85 percent of the cap table. 

“Eventually, we had a few term sheets but one had a clause causing my equity to reset and one VC told me that my cofounder and I were replaceable. When we finally accepted one, the backer folded almost immediately after we signed.”

After CakeStyle didn’t secure funding, Millie changed careers. She left Sandbox Industries and joined AngelList in San Francisco as they launched their Syndicates product. In her role, she matched investors with startups – some good, many misguided. “I spoke with so many bright founders working on ideas that were long shots at best. During this time, I realized that I was passionate about being an entrepreneur and uninterested in the binary outcomes that seem to come along with accepting venture capital.”

Finally, Millie decided it was time she built a startup after several corporate gifting experiences revealed huge disruption potential.

The Problem With Corporate Gifting

Throughout Millie’s career, she’d noticed that buying corporate gifts wasn’t the same as most shopping experiences. Ecommerce sites were well merchandised, user-friendly, and technologically oriented. But to buy swag, she had to make an in-person appointment to see samples and sign off on archaic-looking POs (purchase orders).

Besides lacking focus on customer experience, Millie believes corporate gifting vendors and the companies buying the gifts lack the proper gifting mindset. “Most gifts aren’t thoughtful enough,” she says. “When you give an impersonal gift, people never think of you again. Many of our competitors just send people an email saying they have sent you a fifty-dollar gift card. People feel nothing when you do that.”

“According to the reciprocity principle, if they like your gift, they’ll feel more open to your offer or will at least agree to take the call.”

Millie says corporate gift-giving isn’t just limited to employee swag like mugs and sweaters. It can be used to woo recruits and close sales.

“If you have some leads you’re planning to call, you could send them a gift beforehand. According to the reciprocity principle, if they like your gift, they’ll feel more open to your offer or will at least agree to take the call.”

Early Growth From Great Customer Service

In 2015, Millie quit her job and started a gifting business called Brilliant – one she knew could be profitable without selling its vision to the highest bidder. “I didn’t want to have to raise money, and I already knew a services business builds revenue fast.”

At this point, Millie possessed all the skills of a startup dream. She could do design, sales, software engineering, finance, spreadsheets, and more. She designed a website, found suppliers, and then began growing her clientele by sending emails.

Millie (right) with Brilliant COO Lindsay Cohen.

“Initially we took a scattershot approach to outbound,” she says. “I hired a guy on Upwork to pull email addresses and names for me. He’d bring back a variety of industries and categories. The emerging pattern was that B2B SaaS companies with between 200 and 5,000 employees were our best targets. Their lifetime value tends to be high relative to the cost of gifts.”

Millie’s email campaigns succeeded because she targeted warm leads and always picked up the phone if a prospect reached out.

“I would use my signature at the bottom of the email with my phone number. One time the CMO of ForeSee, Eric Feinberg, called the number and he ended up becoming one of our customers. He told me personally that the biggest deciding factor was that I answered his call.”

These personal relationships at companies later helped Millie retain and grow her customers too. She says one of the metrics she’s most proud of at Brilliant is its Net Revenue Retention which exceeds top benchmarks for VC-backed enterprise companies.

“Early on, our contact at an important client left. We were very worried about the account and wanted to figure out where she had gone. We met the new person who took her spot and found her contact at her new job. We kept her account at the old place and the new place.”

Asset Light to Asset Heavy

Hard work and her swiss-army-knife skill set helped Millie immensely in the early stages of her startup. But, nine months in, she was in deep water with multiple clients, gift suppliers, and logistics companies emailing her around the clock. It was time to make her first hire.

“After my first design hire, I realized not all designers were creatives or had sales chops.”

She decided her first part-time role would need to be a creative partner to manage gift curation, product design, and project management. “We still think of that role as a unicorn because we ask them to do a lot,” she says. “Back then, we’d ask them to know Photoshop, Illustrator, how to sell, how to use Excel, and how to use our homegrown software system.”

Millie says it took a few strikes before she learned how to hire remote workers. “At first I thought the ideal background would be a designer because designers were creative,” she says. “But after my first design hire, I realized not all designers were creatives or had sales chops. They needed to be able to evolve with trends since we’re trying to appeal to picky startups. We ended that contract pretty quickly.”

Another early hire, a much more creative type, quit on his first day. “We hired this one super creative guy,” she says. “At the end of the first day, he put in notice because he wanted more design work and less project management. A few weeks later he sent a thank you and sorry note. Honestly, I loved that guy, he created eight Slack emojis on his one day that were very popular with the team later. We always think of Gabe whenever we use the party parrot.”

The hiring process has gotten easier since then. Today Brilliant employs an entire team of Creative Partners who meet with clients, help with budgets and timelines, source gifts, and design campaigns along with Project Managers who execute the projects

For a few more years, Brilliant’s remote team remained small and Millie operated all warehousing out of her garage. Eventually, she was driven out of her house when neighbors complained about the “light manufacturing activities” in her neighborhood. She then tried and failed to find a third-party warehouse that met her exacting standards for packaging.

“When you get a gift, everything matters, including the unboxing,” says Millie. “That unboxing experience is critical for people receiving curated corporate gifts that attempt to evoke an emotional response or cause certain behavior. We couldn’t have everything in polybags with barcodes on it.”

Millie used her profits to open a warehouse specially designed for packaging goods to the Brilliant standard. 

“I always wanted Brilliant to be an asset-light business, but the opposite of light is a warehouse with a pink pallet jack and rows of heavy racking. However, our VC-backed competition has to stay away from products, services, and warehousing because they want the SaaS multiples. We’re not worried about having our revenue tied to SaaS versus service or products. We’re after a good solid business.”

Scaling to Tech Proportions

Today, Brilliant offers a handful of SaaS products to businesses that want a self-serve gift distribution process. One of these is a tool called Storefront which Millie describes as a simplified Shopify adapted for corporate gifting. It has all of the features like custom currencies, gift cards, and promo codes that corporate clients need to create company stores.

Another major application within Brilliant is Preferred Gift which allows people to send gifts without a mailing address by requesting information via email. On Preferred Gift, customers can create an email list of the individuals they want to send gifts to with a dashboard showing conversion rates and clickthroughs.

Brilliant also integrates with Salesforce, letting employees send gifts from where they sit to leads in their sales funnel. Any HR system can integrate with Brilliant to easily send new hire packages and other employee gifts.

Don’t Start a Business With Your Eyes Closed

While SaaS businesses have been a stable revenue target for Brilliant, slowing venture capital conditions in 2022 made Millie and her team start looking to other verticals. They’ve since added financial services, law firms, and hospitality companies as clients. “We do well with companies with a reasonably sized employee base and management that understands employee engagement,” she says.

Millie is proud of not becoming bedazzled by VC money or selling out her dream. She thinks it’s all starting to pay off as her business scales to larger proportions. While she is not necessarily against VC funding she believes founders need to fully understand what’s at stake when starting a business with outside capital.

“Bootstrapping has put us in a position of strength. It will let us raise on terms we like if we ever do.”

“In what other world do you celebrate giving your company away and getting new bosses?” she says of raising a venture round. “I think VC makes a ton of sense for some people in some situations shooting for the moon, but I don’t think it makes sense for everyone. My advice is to understand the parameters of what you’re signing up for and think through it. Ask yourself, ‘Is that how I want to spend the next five to ten years of my life?’

“Bootstrapping has put us in a position of strength,” she continues. “It will let us raise on our own terms if we ever do. I think there’s a lack of publicity around the alternative.”

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Andrew Gazdecki
Andrew Gazdecki
Andrew is an award-winning serial entrepreneur with three exits. He’s the founder and CEO of MicroAcquire, the world’s most founder-friendly startup marketplace, and its rebellious child, Bootstrappers, which gives voice to the entrepreneurial underdog. When not building businesses, he writes for Forbes, Entrepreneur, and now, Bootstrappers.

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