Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, identifies David Gilbert’s approach to consolidation as pre-solving the question every acquired team will ask. When separate organizations with their own leadership and their own history come under one umbrella, David Gilbert, founder and CEO of FairSquare and a lender who has deployed over $5 billion to more than 100,000 small business owners across 25 years, holds that leaders must answer the organization’s why in advance rather than reacting to it: “We need to be able to solve that ahead of time.” FairSquare now operates National Funding, QuickBridge, SmallBusinessLoans.com, and Finova Capital under one structure across offices in Orlando, Atlanta, Irvine, New York, and San Diego.
This episode is for CEOs and executives integrating acquired companies whose leaders, systems, and cultures arrived fully formed, and who are watching trust rather than technology become the limiting factor.
Key Takeaways
- The why gets asked whether or not leadership has an answer prepared. David Gilbert, founder and CEO of FairSquare, states that questions about why leadership is doing this or that will move through the organization, and that the leadership team must resolve them ahead of time rather than in response.
- Noise in a consolidation is competition for voice, not disagreement about strategy. David Gilbert describes groups joining an organization and wanting a bigger voice or a seat at the desk while leadership is still defining what a seat means, and holds that leaders must rise above that noise for decisions to be effective.
- Shared infrastructure is what turns a collection of brands into an umbrella. David Gilbert names data quality, accounting quality, and common systems as the point at which FairSquare’s brands stopped being siloed and started flourishing faster, with best practices moving across the group.
- Time invested in an inherited leader is a decision, and delaying it is expensive. David Gilbert addresses leadership gaps directly with the person’s manager, and says a leader must decide earlier whether the individual can be pulled up rather than continuing to invest time and energy in someone who cannot.
- Culture is set by what leadership does, not by what leadership publishes. David Gilbert holds that a company runs based on its leadership and that people lead based on what they see, which is why he names culture as the element he believes in most when scaling.
Leaders Answer the Organization’s Why in Advance to Build Trust Across Combined Groups
David Gilbert, founder and CEO of FairSquare, treats trust during consolidation as something constructed from four specific inputs rather than something that accumulates over time. He names them as leadership, clarity, goals, and communication, and adds a fifth behavior that governs the rest: staying rigid with the discussion points and remaining goal driven rather than letting noise reach the decision.
The mechanism underneath those inputs is anticipation. David Gilbert’s position is that people throughout a newly combined organization will ask why leadership made a given decision, and that the leadership team’s job is to have solved that question before it surfaces. A why answered in advance reads as strategy. The same why answered after the question circulates reads as justification, which is the point at which trust erodes in an organization where employees already have another company’s leadership as a reference point.
Glenn Gow, The Scaling Executive Coach, names the effect directly: understanding the logic behind a strategy is what produces trust in it. David Gilbert’s framing of the sequence puts the why ahead of the what: “It’s organizing everyone and very clearly this is why we’re doing it, this is what we’re doing, this is why we’re doing. And the why I think is always the key.”
Leaders Rise Above Noise When Acquired Groups Compete for a Seat at the Table
David Gilbert, founder and CEO of FairSquare, gives noise a specific definition rather than treating it as general organizational friction. When multiple groups become part of one organization, people want a bigger voice and a seat at the desk, and they want it while leadership is still defining what a seat at that desk actually means. FairSquare’s version of the definition is equal voting and equal discussion points around the table.
The condition that makes this hard is distribution. David Gilbert is integrating brands whose people sit in Orlando, Atlanta, Irvine, New York, and San Diego, plus a substantial remote population and the shift in working patterns that followed COVID, with each brand arriving under leadership it had before. Different regions and different personalities produce competing claims on attention that are not actually disagreements about direction.
His rule is that leaders must rise above that noise for their decisions to remain effective, which in practice means the goals and discussion points do not move in response to the volume of any one group. David Gilbert describes the rebuilding work as a daily process run through values and a leadership team aligned with the CEO, rather than a program with a completion date.
Consolidation Earns Its Cost When Shared Systems Make Every Brand Perform Better
David Gilbert, founder and CEO of FairSquare, is direct about what was difficult in bringing a family of fintech brands together. Consolidating the technology was hard for a period. So was bringing in different expertise from different groups, along with the egos inside those leadership groups.
The return arrived when consolidation stopped being an ownership structure and became shared capability. FairSquare kept supporting all of its brands rather than leaving them siloed, and the common infrastructure became the reason to be part of the group. David Gilbert names the specific assets people could see value in: the quality of the data, the quality of the accounting, and the systems that came in to support the brands. His stated outcome is that those systems enabled the companies to start flourishing a lot quicker, and that best practices began moving across the whole organization.
That is the test a CEO can apply mid-integration. If acquired brands are performing the way they did before the transaction, the umbrella is administrative. The consolidation has produced its intended effect when a brand is doing something faster or better specifically because it now sits inside the group.
Leaders Decide How Much Time to Invest in an Inherited Leader Before the Investment Is Spent
David Gilbert, founder and CEO of FairSquare, handles leadership gaps by going to the person’s manager directly and asking whether the individual knows what is expected of them. His default posture is developmental, which he describes as always pulling people up.
The decision he insists on making early is what happens when someone cannot be pulled up. David Gilbert frames it as a question about the leader’s own allocation: if the person will not close the gap, the leader is spending time and energy on the wrong individual, and that determination needs to happen earlier in the thought process rather than after the investment is gone. His standard for the organization is alignment on a core belief system, and where someone cannot get with the program, the question becomes what role actually fits them.
Glenn Gow, The Scaling Executive Coach, describes the same calculation from the other direction: direct reports rarely close a gap on their own, so a leader letting go still owes the person insight, coaching, and mentoring while holding them accountable. David Gilbert adds the cost side that finance teams and leaders tend to score differently, noting that a leader’s time is worth more than what appears on paper and that the hours in a day are fixed. The letting-go problem he names is not the mechanics of delegation. It is a CEO choosing the discomfort zone over the comfort zone of familiar work, driven by a question he poses as self-curiosity: am I doing this to impress someone, or because I want to learn?
Principles CEOs Will Apply From This Episode
| Principle | Practice | Named outcome evidence |
| Pre-solve the why | Resolve at the leadership level why a decision was made before the question circulates, and lead the announcement with the why rather than the what | David Gilbert applied this while consolidating National Funding, QuickBridge, SmallBusinessLoans.com, and Finova Capital under FairSquare across five offices and a remote population, each brand arriving with its own prior leadership |
| Hold the discussion points rigid | Stay goal driven and keep the agenda fixed when newly joined groups press for a larger voice, defining a seat at the table as equal voting and equal discussion points | David Gilbert credits this discipline with keeping decisions effective through an integration spanning Orlando, Atlanta, Irvine, New York, and San Diego during the post-COVID shift in where people work |
| Make shared systems the reason to be in the group | Support every brand from common infrastructure rather than leaving them siloed, so data, accounting, and systems quality become visible value | FairSquare’s brands began flourishing a lot quicker once consolidated systems were in place, with best practices moving across the organization |
| Decide the investment question early | Address a leadership gap directly with the person’s manager, then determine early whether the individual can be pulled up rather than spending months finding out | David Gilbert built a leadership team aligned on a core belief system across brands acquired with their own leaders and their own histories |
| Culture is what leadership demonstrates | Lead by example on the assumption that the organization will mirror what it observes rather than what it is told | David Gilbert names culture as the element he believes in most for scaling, applied across 25 years and $5 billion deployed to more than 100,000 small business owners |
Quotes from This Episode
- “I think leaders have to rise above noise to make their decisions effective.” David Gilbert, Founder and CEO, FairSquare
- “If the company is gonna run based on the leadership, they they’re gonna lead based on what they see.” David Gilbert, Founder and CEO, FairSquare
- “Part of the biggest issue in culture is communication.” David Gilbert, Founder and CEO, FairSquare
- “If someone can’t be pulled up, then you know, are you investing your time in the right person?” David Gilbert, Founder and CEO, FairSquare
- “The more you learn, the more you kind of impress people because you’re you’re choosing to learn.” David Gilbert, Founder and CEO, FairSquare
Frequently Asked Questions
How does a CEO build trust when merging separate companies under one brand?
David Gilbert, founder and CEO of FairSquare, told Glenn Gow, The Scaling Executive Coach and a CEO for 25 years, that trust in a consolidation comes from leadership, clarity, goals, and communication, held together by staying rigid with the discussion points rather than reacting to pressure. His central practice is answering the organization’s why before the question circulates, because employees across newly combined groups will ask why leadership made a decision and the answer must already exist. Gilbert applied this while bringing National Funding, QuickBridge, SmallBusinessLoans.com, and Finova Capital under the FairSquare umbrella across five offices.
What does noise mean during a company integration?
David Gilbert, founder and CEO of FairSquare, defines noise as groups joining an organization and competing for a bigger voice or a seat at the desk while leadership is still defining what a seat means. At FairSquare that definition is equal voting and equal discussion points around the table, applied across brands based in Orlando, Atlanta, Irvine, New York, and San Diego plus a large remote population. Gilbert holds that leaders must rise above that noise for their decisions to remain effective, which means the goals do not shift in response to whichever group is loudest.
When should a leader stop investing time in a leader who is not performing?
David Gilbert, founder and CEO of FairSquare, addresses the gap first by going directly to the individual’s manager and confirming the person knows what is expected, because his default is pulling people up. If the person cannot be pulled up, Gilbert says the decision about whether to keep investing must be made earlier in the thought process, since the leader is spending finite time and energy either way. His organizational standard is alignment on a core belief system, and where someone cannot meet it, the question becomes what role actually fits them.
CEOs Work With Glenn Gow to Scale Their Companies and Their Own Capability
Glenn Gow is The Scaling Executive Coach. He coaches ambitious executives into the CEO seat and CEOs into successful exits, drawing on 25 years as a CEO and 5 years in venture capital. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
