From Small Acquisition to $30m Industry Leader - Acquiring Minds

Acquiring Minds — Episode Summary

Episode: From Small Acquisition to $30m Industry Leader

Host: Will Smith
Guest: Robin Kovitz, Owner of Baskets (with an “i”)
Date: April 2, 2026

Episode Overview

In this episode, Will Smith interviews Robin Kovitz, an entrepreneur who transformed a small Toronto-based gift basket business into a $30 million industry leader. Kovitz shares her unconventional path from a third-generation family business background to investment banking, Harvard Business School, and ultimately entrepreneurship through acquisition. She discusses the challenges of finding the right business, her approach to balancing ambition with family, why she believes in long-term business ownership, and her methodical scaling of “Baskets” both organically and through acquisition.

The episode is rich with practical insights for self-funded searchers, women in search, and anyone contemplating buying and growing a business for the long haul. Topics ranged from finding the right business, developing non-negotiables, the reality of buying a small unpolished business, operating in a “niche” industry, the importance of loving your business, and structuring for long-term, values-driven growth.

Key Discussion Points & Insights

Robin’s Background and Family Business Influence

Third-Generation Entrepreneur: Robin began on the hamburger assembly line at age 14 in her family’s meat business. This early ground-level experience deeply shaped her appreciation for every role in a business.
Exposure to Reality of Entrepreneurship: Watching her father experience “the good, the bad, and the ugly” of business ownership—bankruptcy threats, industry turmoil, then a major exit—left Robin both inspired and cautious about small business ownership.
- “I've seen from the hardest of the hard to the highest of the High in my dad's experience as an entrepreneur. And that terrified me. I wanted to work for Steady Eddie bank for a while.” — Robin (07:16)

Path Through High Finance & Private Equity

Pursuit of Stability: Robin initially pursued investment banking and private equity for financial stability and an education her father never had.
Private Equity Lessons: She noticed high deal multiples and increased competition as “a losing game,” which inspired her to seek opportunities in smaller businesses.

The Pivot to Entrepreneurship & Search

Motherhood & Career Constraints: As Robin faced starting a family, she realized investment banking hours clashed with being the kind of mother she wanted to be. This spurred the idea of buying a small business for more autonomy.
Early Search Era: Robin’s search predated the now-standard “search fund” and “self-funded search” nomenclature, learning by trial and error—eventually taking four years to find her business.

Search Details & Lessons

Self-Funded Searcher: Used family resources, home equity, and friends rather than raising a formal fund.
Resilience in Lengthy Search: Robin’s four-year search is now a “cautionary tale” in ETA circles, but she embraces it:
- “Tell them it's four [years]. I'm not embarrassed. This is, it just is what it is… you’re going to look back in 15 years… to focus on what matters and that's finding a great business.” (34:05)
Personalized Search Approach vs. “Spam” Tactics: She focused on building genuine relationships: “I put the baby in the car, started driving around, finding industrial parks… started, like, dropped off my printed brochure and was like, ‘Hey, well, I kind of want to be an entrepreneur like you…’” (51:30)

Defining a “Great Business” — The Three Non-Negotiables

1. Low Customer Concentration

“Customer concentration is number one… your business can disappear overnight.” (37:52)

2. Recurring Customers / Repeat Purchases

“I have this database that repeats and that's valuable, that has long term value… a business where you have an existing customer base that orders from you frequently is absolutely non negotiable.” (38:48)

3. Highly Scalable

Robin wanted the business to be “something I could grow… do these tuck-under acquisitions, platform it together and be bigger.” (41:46)

She encourages searchers to identify their own “three non-negotiables,” likening it to prioritizing qualities in a life partner—narrowing focus leads to action.

Long-termism & B Corp Philosophy

Permanent Ownership Mindset: Robin explicitly rejects the private equity “flip in 5 years” model. Her intent is to own, grow, and possibly never sell the business—echoing the family business legacy.
- “I have no interest in selling the business… I don’t know any entrepreneur who can really generate long-term value in [5-7 years].” (24:03)
B Corp Mission: Baskets is a certified B Corp, reflecting Robin’s dedication to fair wages, ethical supply chains, and balancing profit with stakeholder value.
- “I believe that business can be done differently. Can you be a better stakeholder? Can you do business differently, help everyone rise?” (26:57)

Industry Choice & “Niche Domination”

Misjudged Market Size: Many see gift baskets as a tiny “mom-in-the-basement” business. Robin realized it’s an unusually large, fragmented, and complex industry once you look more closely (“the kindness industry”). (46:29)
Fragmentation as Opportunity: Complexity and low barriers allow many to reach $1-3M in revenue, but scaling beyond that is hard—Robin’s business stands out due to sophisticated operations and tech.

The Acquisition – Deal Dynamics & Turnaround

Deal Structure: Acquired Baskets after a co-founder dispute led to a shotgun buyout; Robin ensured majority control and negotiated two parallel deals due to friction.
Reality Check: Discovered the business was “so much worse than expected”—no processes, no data, no systems (“I had to teach everyone what a contact list is”). (60:49)
Key Takeaway: Over-fund your deal; expect surprises and the need for a “what if”/rainy day fund. (68:04)

Scaling Up — Facilities, Team, Systems

Growth Playbook: Robin hits recurring cycles of upgrading facilities, building leadership teams, and investing in systems (ERP, e-commerce).
- “I always say it’s like juggling or whack-a-mole… you get to do it all over again. … Facilities, team, systems. I'm like in this recurring nightmare.” (73:01)

Pivot to E-Commerce & B2B / B2C Split

Early founders of Baskets were web pioneers; Robin accelerated online and consumer strategy.
COVID acted as a major catalyst, rapidly building out the D2C side; today, business is roughly 50/50 B2B and D2C. (75:06)

M&A and Roll-Up

Five Acquisitions: Since 2018, Robin has acquired five other gift basket businesses as a growth strategy—absorbing best practices from each.
- “The customer list for sure is sticky, but there's usually something else special about these little businesses… my mission is trying to figure out what that is and then preserve it.” (87:04)
Brand Consolidation: Moving toward a unified “Baskets” brand, but careful not to “cyborg” unique cultures or strengths away.

Differentiation: Money Back Guarantee

Robin introduced a rare money-back guarantee as a mark of her company’s quality and to permanently distance Baskets from “bad actors” in the industry. (79:13)

Women in ETA & Canadian Perspective

Robin is now a role model for women in search/founders seeking work-life balance and ambition. She shares the challenges and changing climate for women raising capital and building businesses in Canada.
She encourages aspiring Canadian entrepreneurs: “If there's opportunity in US, there's just as much opportunity in Canada… such an opportunity for young people to come in and define their next chapter.” (91:01)

Notable Quotes & Memorable Moments

On Industry Choice & Love:
“If you are all in all the time as an entrepreneur, you need to love it or otherwise you're going to hate it.” — Robin (97:20)
On Search Length:
“Tell them it’s four [years]. I’m not embarrassed… focus on what matters and that’s finding a great business.” — Robin (34:05)
On B Corp and Stakeholder Value:
“Can you do business differently, help everyone rise? That’s something that I’m toying with, with long term value.” — Robin (26:57)
On Buying Small Businesses:
“The skill sets of running a $100 million business are very different than running a $2 million business.” — Robin (20:03)
On Building Through Acquisition:
“From each of these acquisitions, we gain something. So I still have their head of design from the first business we bought, who has completely changed the look and feel of our company…” (87:04)
On Over-funding a Deal:
“Over-fund the deal. No matter what you do, have $250K that just is the what-if bucket.” (68:04)
On Search Personalization:
“I put the baby in the car, started driving around, finding industrial parks… dropped off my printed brochure and was like, ‘Hey, I kind of want to be an entrepreneur like you…’” (51:30)

Timestamps for Important Segments

| Timestamp | Topic | |:---------:|:------| | 05:36 | Robin’s early family business experience | | 12:02 | Decision to leave finance and seek entrepreneurship | | 15:16 | Heard about “buying small” businesses pre-search fund era | | 19:45 | Early search, self-funded approach, lessons from Rick Ruback/HBS | | 23:12 | Motivation for long-term ownership vs. flipping | | 26:57 | Explanation of B Corp and values-driven business | | 34:05 | On her four-year search and searcher anxiety | | 35:25 | Framework for defining a “great business” – 3 non-negotiables | | 46:29 | Market size and complexity of gift baskets business | | 51:30 | Personalized search tactics vs. spam approach | | 60:49 | Turnaround realities—lack of systems, tough integration | | 68:04 | Cash constraints and advice to “overfund” the deal | | 73:01 | Scaling playbook: facilities, team, systems | | 75:06 | Shifting Baskets from B2B to D2C/COVID acceleration | | 84:21 | M&A roll-up strategy, integrating acquisitions | | 91:01 | Robin’s perspective on ETA opportunity in Canada | | 97:20 | The importance of loving your business | | 98:24 | Find and dominate overlooked industries |

Final Thoughts

Robin’s story showcases a long-game approach to business acquisition—rooted in passion and operational excellence rather than quick returns. Her willingness to go slow, make mistakes, and build for permanence is a compelling model for entrepreneurs who want “their life’s work” to have lasting impact.

For women, self-funded searchers, and anyone aiming to blend family and ambition, Robin’s journey is both a practical guide and an inspiration.

For More Information

Guest: Robin Kovitz — Baskets (with an “i”)
Host: Will Smith — Acquiring Minds Podcast
YouTube: Acquiring Minds channel