Taylor Wallace, Tyler O'Connor·October 3, 2024

Why Sell to Private Equity: Former Guest Has an Exit | Taylor and Tyler Update Interview

This update episode features two returning guests. Taylor Wallace, a former tech worker who partnered with a friend to buy and operate doggy daycares in Tampa, recounts how they grew from 2 to 4 locations before selling to Pet Resort Hospitality Group (backed by Trivest) in fall 2023 as part of a multi-brand rollup now operating 20 units. Their thesis — buying underutilized facilities and doubling dog capacity through better operations and marketing — worked on the first two acquisitions, producing a 5x return on invested capital in ~4 years, but growth stalled as they struggled to replicate early wins at scale without PE-level capital. Taylor now serves as Head of Marketing and Strategy for the combined platform. Tyler O'Connor, a former Army officer turned consultant who bought Bird Golf Academy 23 months prior, gives a grounded update on a premium, project-based golf instruction business (~$3.6m revenue, 20+ locations, all instructor-travel model). Revenue fell short of the seller's $4–4.5m projection, likely inflated by post-Covid travel demand; Tyler identifies owner-dependency in sales, seasonal cash flow, and the underestimated hospitality dimension as the key ongoing challenges, while noting resilience when the key Phoenix location partnership collapsed and was quickly replaced with a better one.

Deal facts

purchase price: First acquisition: high six figures (shy of $1m); second acquisition: low seven figures
revenue: Bird Golf Academy: ~$3.6m projected for year (originally projected $4–4.5m at acquisition)
financing structure: Taylor: blend of debt and equity (specifics not disclosed); Tyler: SBA implied, working capital included at purchase
notes: Taylor Wallace: grew from 2 to 4 locations independently, then joined Pet Resort Hospitality Group (backed by Trivest) in fall 2023 as part of a multi-company rollup; achieved 5x multiple on invested capital in ~4 years. Tyler O'Connor: bought Bird Golf Academy using ~$100k; business had ~20 locations (all instructor-travel model, no owned real estate); 23 months into ownership at time of recording.

Why this business

Taylor: A best friend who managed a franchise doggy daycare and Taylor's own tech/marketing background converged after Covid layoffs; they saw an opportunity to buy underutilized facilities and double dog capacity through operational and marketing improvements. Tyler: His mom told him he didn't have to buy a boring business — he searched 'golf' on BizBuySell at 10pm on a Monday and found Bird Golf Academy; his passion for golf combined with a business that needed a better operator.

What's working

Taylor: thesis of buying underutilized doggy daycare facilities and doubling dog capacity through operational improvements (partner's expertise) and lead generation (Taylor's marketing/tech background) proved out on first two acquisitions
Taylor: joining Pet Resort Hospitality Group (Trivest-backed) provided capital scale, a management team, platform synergies (bulk purchasing of supplies, better marketing rates), and a denovo strategy with a dedicated head of real estate
Taylor: achieved 5x multiple on invested capital in approximately four years
Taylor: PE partnership allowed de-risking of illiquid equity while retaining upside and staying operationally involved
Tyler: business is operationally resilient — when the key Phoenix golf course partnership ended (40% of revenue), Tyler quickly secured a better replacement location with better margins
Tyler: raised prices annually while slightly reducing student count, keeping top-line revenue roughly flat year-over-year
Tyler: deliberately structured a general manager buffer between himself and 1099 instructors to manage complaints and preserve relationships
Tyler: improved customer communications (pre-school reminder emails, packing lists) reduced inbound complaints
Tyler: secured a creative TV advertising deal — $75k of TV time in exchange for golf schools from a former student who is an ad executive

What's hard

Taylor: denovo construction took two years instead of the expected six months — lacked real estate development expertise and wrong partners from the start
Taylor: growth stalled as they became too picky after early successes; investors' risk appetite didn't match founders' ambition; smaller acquisition targets offered limited upside
Taylor: larger multi-unit sellers weren't taking them seriously without PE-level capitalization
Tyler: business revenue came in well below the projected $4–4.5m at acquisition; running closer to $3.6m — likely inflated by post-Covid travel demand at time of sale
Tyler: highly project-based, non-recurring revenue means every lead matters and revenue is sensitive to the owner's sales attention; a period of travel caused a 2% revenue decline
Tyler: owner-dependency in sales — Tyler is the primary salesperson and when unavailable revenue drops
Tyler: managing 1099 instructors who resist change (e.g., adoption of launch monitor technology); some instructors are resistant to new requirements
Tyler: seasonal cash flow — spring is peak, summer and winter are slow; as a first-time owner he overspent early working capital not fully anticipating the need to husband cash through low seasons
Tyler: underestimated the hospitality dimension of the business — customers expect a travel experience, not just instruction

Notable quotes

We would go in and we'd buy a location that had you know call it half the number of dogs we thought we could get in there both from an operation standpoint and a marketing standpoint and he would focus on how do we do that safely and I would focus on how do we actually get the dogs to show up.

A friend I was kind of talking to that's done a lot of deals framed it really well is like you've kind of earned the money at that point but it's in this illiquid asset so do you want to keep it in that illiquid asset or do you want to trade that for cash and equity in another asset.

We joke now that my partner and I the next business we work on is going to have no real estate and no humans.

There are days in small business ownership that will feel like that — your feet are stuck in concrete but your legs have turned to jelly. I'm not exaggerating when I tell you that. You have to be ready for that.