Brand Presence In The Future

The pivot you fear is your only leverage. That is the lesson David Downing, CEO and co-founder of Chipmonk Baking, brought to this episode of The Longer Game, and it explains why his small cookie company kept growing while supply chains, labor markets, and ingredient costs fell apart around him.

Host Michael Maher and David Downing talked through what brand presence actually requires in a market that will not sit still, and the answer had less to do with marketing tactics and more to do with a willingness to change course fast.

From An Apartment To A Commercial Bakery

Chipmonk Baking started in 2019 when David Downing's roommate and now business partner, Jose Hernandez, developed low carb, sugar-free cookies to manage his type 2 diabetes. David Downing liked them enough to build a company around them. Today Chipmonk sells direct to consumer, on Amazon, on walmart.com, and increasingly through wholesale, with a team of nine running a real commercial bakery.

Winning One Independent Store At A Time

Rather than chasing national chains first, Chipmonk built its wholesale business by calling small, independent specialty food stores directly, often reaching the owner on the first call. David Downing explained that this slower, relationship-driven approach paid off in ways he did not expect.

"Often the buyers for larger chains will shop there, because they're looking for like the next small, emerging brand."

— David Downing, CEO and Co-Founder at Chipmonk Baking

That strategy eventually led to a placement with Central Market, a ten-store Texas chain, where order sizes jumped from a case or two to full pallets. David Downing also found unexpected traction in underserved keto markets in the Midwest, where demand existed but competition did not.

When Supply Chains Force Innovation

The clearest test of Chipmonk's adaptability came when the price of its core sweetener, allulose, roughly doubled and then became nearly impossible to source at all. Since it is used in every product, David Downing faced the real possibility of shutting down production entirely.

"We ended up discovering there's a syrup version of allulose which is just literally water and allulose. We use water in our cookies already... and we survived."

— David Downing, CEO and Co-Founder at Chipmonk Baking

That same pressure pushed David Downing to re-examine ingredient costs he had never questioned before, including a supplier switch that cut one input cost by 40 percent simply because his team finally looked for alternatives.

Why Being Small Was An Advantage

David Downing made a point that runs against conventional wisdom: being a small brand during a period of constant disruption was an asset, not a liability. A billion-dollar company with shareholders and layers of process cannot pivot as fast as a nine-person team that has to solve a problem today or lose the business tomorrow.

"If we were a billion-dollar company, there's no way we could move quickly enough to kind of deal with the new realities that we're facing."

— David Downing, CEO and Co-Founder at Chipmonk Baking

Michael Maher connected this to a broader principle for brand owners: difficulty is not the obstacle to growth, it is frequently the mechanism for it. Constraints force a level of scrutiny and creativity that comfort never demands.

What This Means For Brands

• Build relationships with small, independent retailers before chasing national chains. Loyal regional buyers create word of mouth that big placements alone cannot.
• Treat every rising cost as a prompt to re-audit inputs you have not questioned in years.
• Do not assume bigger is always safer. Smaller teams can often react faster to supply chain and labor shocks.
• Expect pricing conversations to get uncomfortable before they get necessary. Waiting too long to adjust prices can hurt more than the conversation itself.
• Use disruption as a forcing function for operational improvements you were putting off anyway.

David Downing's approach to brand building is not glamorous, but it is durable: get the fundamentals right, stay close to your numbers, and treat every disruption as a reason to get sharper rather than a reason to freeze. Watch the full conversation with David Downing and Michael Maher for more on building a resilient brand in an unpredictable market.