Over the years, I have learned that progress rarely comes from waiting for perfect conditions. It comes from recognizing when something is not working, stepping back to understand why, and choosing to act with intention.

That lesson has shown up repeatedly in my work and in my life. I have experienced firsthand how easy it is to become deeply immersed in the day-to-day, solving what is immediately in front of you without taking the time to assess whether you are addressing the right problem. When you are close to the work, activity can feel like progress even when it is not.

What creates movement is perspective. The ability to pause, see the situation clearly, and decide what matters most. When that clarity emerges, action follows naturally and confidently.

I saw this play out in very real ways during COVID-19 while serving as Deputy Mayor of Scarsdale. As medical professionals focused on first-order public health challenges, my responsibility was to help ensure that local businesses could survive. That meant acting quickly, revising codes to allow outdoor dining, launching the community tent, and authorizing sidewalk sales so businesses could stay afloat. The focus was on responding decisively to what businesses needed in that moment.

From the earliest days of TAP, well before my time in public office, I saw the same pattern repeat itself. When business owners feel stuck, it is rarely a lack of ambition. More often, they are too close to the problem to see it clearly, reacting instead of diagnosing. That insight shaped what became the Deep Dive program.

When we first launched the program, it was an 8 month program called the Strategic Advisory Program. It was modeled after the Bain consulting approach, with the intention of bringing disciplined, project based methodology from Wall Street to Main Street. At the same time, we recognized that long term horizons, which are well suited to corporate America, are often misaligned with the realities small business owners face. To be effective, the model had to be adapted to meet entrepreneurs where they were, balancing rigor with immediacy and practical decision making.

In 2020, urgency reshaped the program again. We condensed it into an intensive 2 month format while preserving its core structure. Since our inception, TAP has completed 539 Deep Dive programs.

Why the Deep Dive works

The Deep Dive was built from experience. After years of working alongside entrepreneurs, I learned that real progress requires more than advice or a one time conversation. Business owners need space, structure, and trusted partners to see what is happening beneath the surface.

The Deep Dive is designed as a multi-session engagement. Over various sessions across 2 months, business owners work with 2 experienced consultants to address a specific challenge. We begin with a scoping session to assess readiness and clarify the real issue at hand. The challenge first identified is not always the root cause. This early work separates symptoms from drivers and defines clear deliverables so expectations are aligned from the start.

The two consultant model is intentional. Typically, one consultant brings financial expertise and the other marketing or operational insight. Working as partners, they offer complementary perspectives and consistent support. When relevant, we also bring in an industry expert as a third partner or pair business owners with consultants whose backgrounds directly align with their sector. This flexibility ensures guidance is both contextually informed and immediately applicable. Business owners value the diverse viewpoints, which lead to sharper analysis and stronger decisions.

The Deep Dive is a beginning, not an end point. We follow up at 3 to 6 months and again at 12 months to stay present as new challenges and opportunities emerge. This approach is grounded in long term relationships, not transactional interactions.

Shaped by the voices of business owners, partners, and consultants, and informed by field insights, the Deep Dive reflects a commitment to meeting entrepreneurs where they are. It is the result of twelve years of listening, learning, and refining how we support small business owners.

What we hear from the field

One of the most consistent truths I have learned is how lonely entrepreneurship can be. Even strong, capable business owners often lack access to true peers, strong networks, and the right resources to share the weight of decision-making.

In a short video, we hear a candid reflection on the realities of entrepreneurship and the value of a trusted perspective.

Mark Caserta, Vice President of Programs at the Brooklyn Chamber of Commerce, puts it plainly:

As Mark clearly states, entrepreneurs do not just need access or information. They need perspective. They need someone who can sit beside them, listen closely, and help them see their business more clearly.

That moment of clarity is often what allows momentum to return.

A Deep Dive in action: HiFi Provisions

The need for perspective Mark describes is one he has seen repeatedly in his work alongside small business owners. It is not theoretical. It shows up in real time, often when founders are doing many things right but facing decisions that will shape what comes next.

HiFi Provisions, a Brooklyn-based vintage records store, was referred to TAP through the Brooklyn Chamber of Commerce in connection with Brooklyn Alliance Capital at a moment when focused, strategic guidance could support thoughtful decision-making and long-term resilience.While the business entered the Deep Dive with strong fundamentals, including a well-defined brand, a compelling product, and deep founder expertise, it was navigating familiar pressures: rising operating costs, increasing competition, and the challenge of translating steady sales into sustainable profitability.

The Deep Dive created space to step back and focus on the decisions that matter most. Working alongside two TAP consultants, HiFi is refining its pricing strategy to improve profitability, evaluating mission-aligned funding pathways, and assessing whether its operating structure best supports long-term sustainability.

This kind of clarity is what the Deep Dive is designed to deliver. Across the program, 93% of Deep Dive businesses remain open one year post-engagement, 90% report job creation or preservation, and 93% report increased confidence, a critical driver of long-term growth.

HiFi’s work is ongoing, but the goal is clear: make informed decisions with confidence and move forward with intention.

From clarity to confident action

This work does not happen in isolation. The small business support ecosystem is often fragmented, and entrepreneurs are frequently asked to navigate it alone. When trusted partners identify a gap and connect business owners with the right support, impact accelerates.

TAP brings structure, expertise, and a mindset rooted in decisive action. Our partners bring context and trust. Together, we help business owners step back, see clearly, and move forward with confidence.

That is the work we will continue to do alongside trusted ecosystem partners to help entrepreneurs turn clarity into momentum and momentum into growth.

✨ Apply today for a free 1:1 consultation or partner with us to help small business owners turn challenges into breakthroughs.