THE FOUNDER FILE
ADAM ROSS ● BANKING → BUILDING ● HEYDAY CO-FOUNDER ● A CUSTOMER GETS THE LAST WORD ●
PERSON / FOUNDERS & OPERATORS01 / THE SMALLER BET

Adam Ross and the art of the smaller bet

Before co-founding Heyday, Adam Ross learned to admire the people across the banking table. Building his own businesses meant learning when to stop debating and ask a customer.

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Adam Ross had a sensible precaution for leaving investment banking: see whether anyone wanted the shoes. Before committing to Soludos, the footwear business he co-founded, he took samples to 30 accounts. Almost all offered informal purchase orders. A career change looked rather less mysterious with prospective customers attached. The entrepreneurial leap had acquired a handrail.

He describes himself as risk averse. That admission makes his later career more interesting. Ross helped build Heyday, a facial shop business that began in New York in 2015 and subsequently expanded through franchising. The thread connecting shoes and shop chairs is a preference for finding out what people will actually buy before getting too attached to a theory.

The other side of the table

Banking gave Ross a close view of established consumer companies. He went into mergers and acquisitions after university, and his work included the sale of Gillette to Procter & Gamble. Food and beverage, beauty and confectionery were among the sectors he covered. He had access to large transactions and the people responsible for them.

Over time, the smaller deals became more attractive. Entrepreneurs arrived with businesses they had built and stories about getting them there. Ross wanted a more direct part in that process. An adviser can help a company make a consequential decision; a founder has to live with the ordinary decisions that follow it, from product to price to the first disappointed customer.

His route to Heyday also included a brunch in Los Angeles, where friends complained about getting facials. The complaint was commercially useful: a service people wanted had become inconvenient to buy. Ross had spent years looking at consumer businesses from the financial side. Here was a chance to examine one from the customer's chair.

A banker needs someone who can draw

Michael Pollak brought architecture, branding and design to their partnership. Ross brought the banking background. Pollak took responsibility for shaping the experience inside Heyday's shops, giving the business a second way of seeing the same problem. A spreadsheet could explain the cost of a room; design could help explain whether someone wanted to enter it.

Heyday co-founders Michael Pollak, left, and Adam Ross, right, standing outside a shop
Two founders, one dress code. Michael Pollak (left) and Adam Ross, photographed for their 2019 Hurdle conversation. Photograph via Hurdle.

The division of responsibilities mattered because Heyday depended on people and physical space. By 2021, the leadership team also included Sean Bock, whose background included developing Drybar's franchise business. Ross was assembling experience from adjacent consumer services rather than assuming banking supplied every answer.

His argument for the workforce was practical. Heyday employed its estheticians, offered a two-week onboarding programme and provided continuing education support. Training and development were part of the proposition. The person delivering the service would determine whether the carefully designed room ever earned a second visit.

The customer gets a vote

Ross has been unusually candid about an expensive founder habit: spending too long around a boardroom table debating what customers want. He recognises it from his own career. An intelligent room can produce a great many arguments without producing a single purchase. Customers have the inconvenient advantage of being able to settle the matter.

That lesson shaped his approach to marketing. Heyday concentrated on a defined customer group and invested in the experts providing the service. A personal experience could create advocacy without requiring every interaction to become an advertisement. Recommendations from someone you trust have a different texture from a campaign designed to announce that trust is available.

His advice to younger people follows a similar resistance to external scoring. He encourages them to judge success through their own lens. Coming from someone trained in finance, that is an interesting instruction: choose your measure before allowing somebody else to hand you a league table.

“We should judge success through your own lens”

Adam Ross, 2020

In a later conversation with Kara Goldin, Ross described small hospitality improvements, including access to a phone charger, that could round out a visit. They were useful precisely because they were ordinary. A customer arriving with a dying battery may have a more immediate ambition than participating in a founder's grand theory of retail.

He also remembered the early shops opening from seven in the morning until ten at night, with the busiest stretch running from five until ten. Convenience became a decision about opening hours. The business had to fit around customers' days. An elegant proposition loses some of its charm when its door is locked at the only hour you can visit.

One hundred promises to open

Heyday's next challenge was reproducing the experience away from its original market. Ross supported franchising because he wanted local owners invested in the daily work. In a business built around appointments, staff and repeat visits, the distance between a head office and an individual shop can become surprisingly large.

In 2022, he reported that Heyday had sold more than 100 franchise units in an eight-month period during the previous year. Those were agreements for future shops. They represented commitments and work ahead, with leases, hiring and openings still to come. The distinction matters in a business where the customer ultimately needs an actual door.

THE EXPANSION MOMENT / REPORTED IN MARCH 2022100+

Franchise units sold in eight months during 2021.
Agreements for shops, rather than a count of open locations.

The first franchisee-owned location opened in Bethesda, Maryland, in 2021. The model was moving from a plan into a place. Ross also reported that monthly members accounted for roughly 70 percent of treatments by the end of that year. Recurring visits were becoming central to how the shops worked.

That gave expansion a second obligation. A brand could persuade someone to visit once through curiosity. A membership asked the shop to remain worth returning to. Every repeat booking was a fresh decision, however tidy the recurring revenue might look on a slide.

The argument for fewer doors

For someone overseeing expansion, Ross could sound remarkably restrained about distribution. In late 2022, he described hearing another business celebrate going into 1,700 Target stores. His instinct was to prefer 100 or 200 at first, using the smaller footprint to learn and improve execution before committing to something broader.

The advice he offered companies short of capital was to prove their concept through customer and market depth. A suitable investment partner could extrapolate from that evidence. It was a recognisable continuation of the shoe samples: give an idea enough contact with the market to deserve the next commitment.

Heyday raised a $12 million Series B extension that year, led by existing investor Level 5 Capital Partners. Ross treated fundraising as a second job running alongside the first. Experience in mergers and acquisitions helped with the process. It did not remove the ordinary difficulty of running a company while asking people to finance its future.

A founder makes room

In June 2023, Heyday appointed Andy Taylor as CEO after a year-long search. Taylor arrived from Levain, bringing experience growing a retail business across markets. Ross and Pollak remained board members, continuing to work with him on product development and retail growth.

The handover changed Ross's relationship with the company he had helped start. The daily executive responsibility moved to another person; the connection to its direction remained. His public support for Taylor emphasised culture, people and the operational demands that accompany expansion.

There is a fitting detail in that choice. Earlier in his career, Ross had wanted to move closer to building a business. By this stage, helping the business develop included choosing someone else to run it. A founder's influence can take several forms over time. Holding the same title is only one of them.

2015First Heyday shop opens in New York
2021Franchising begins; Bethesda opens
2023CEO handover; Ross remains on board
2025Joins goGLOW as a strategic advisor

The quieter version of ambition

Asked to describe himself in 2023, Ross chose diligence and loyalty among his qualities. His emphasis was on persistence, showing up and doing the work. Those are modest words for a founder interview, where the temptation to sound like a launch announcement must be considerable.

His account of success also allowed room for difficulty. He looked for meaning and fulfilment in a week, rather than assuming a good week had to be an easy one. He wanted to improve communication with his team and find more balance. The ambitions were personal and unfinished, which made them sound like ambitions a person might actually have.

The later career widened his scope again. Wharton's 2024 account of his work included board roles at Heyday and Serena & Lily and a senior partner role at Protea. It also recorded his undergraduate education at the University of Sydney, Wharton MBA and CFA charter. Finance remained part of his equipment.

In April 2025, goGLOW announced Ross as a strategic advisor. Founder Melanie Richards was building a sunless tanning business, giving him another setting for his interest in consumer experiences and expansion. His explanation centred on working with talented, ambitious people and creating relationships that carried beyond a transaction.

He has also discussed his work with Front Street Equity Partners, returning to questions about emerging brands and franchise growth. The work now includes helping other founders think through the decisions he once faced himself. His career began with a desire to cross the banking table. These days, he has experience worth bringing to either side.

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