There’s a reason the question-mark suit became a cultural icon: it stood for permission. Permission to ask better questions, to find resources hiding in plain sight, and to stop leaving opportunity on the table. In my conversation with Matthew Lesko—yes, the “question mark guy” whose career spans over 50 years of helping everyday Americans access billions in government and community funding—I heard a message every business executive needs right now: in uncertain times, resilience isn’t just a mindset. It’s a system. And that system is powered partly by capital markets—and partly by an entire “community economy” that many leaders never learn how to use.
As executives, we love efficiency, speed, and the elegant simplicity of a market solution. But when you ignore the other 40% of the economy—government and nonprofit capital and services—you’re playing with one hand tied behind your back. Lesko’s career has been spent removing those knots. What he teaches is unglamorous and wildly effective: how to find the right door, talk to the right human, and unlock non-dilutive resources that stabilize families, safeguard employees, and scale businesses without bleeding equity.
Below are three takeaways from Matthew’s journey that matter for modern leadership—and how to operationalize them inside your company. These are pragmatic, phone-in-hand steps. If you want to build a more resilient business, this is your field guide.
Takeaway 1: There’s More Than One Economy—Intelligent Leaders Use Both
One of Matthew’s most clarifying insights is visual: if you graphed the U.S. economy, roughly 60% is private-sector capitalism—and 40% is what he calls the “community economy,” made up of government and nonprofit organizations that exist to give, not sell. That 40% funds fire departments without asking for your credit card, provides workforce training, subsidizes childcare, underwrites innovation, helps pay rent in crises, and, critically for business leaders, buys goods and services through contracts of every size.
Executives tend to over-index on the 60%. We type our needs into Google, get a funnel of paid results, and purchase solutions. That works—if you have budget. But public-sector and nonprofit resources don’t show up in Google ads. They aren’t optimized to sell. They’re designed to serve. To reach them, you don’t window-shop; you actually talk to people.
Here’s the leadership imperative:
- Stop assuming what you need must be purchased. First ask: is there a community-funded path?
- Institutionalize a “dual-track” operating habit: for any strategic need, explore private options and community-funded options in parallel.
Practical moves for executives:
- Establish “Community Capital Ops” as a function in Finance or Strategy. Charter it to identify, pursue, and manage government contracts, economic development incentives, and nonprofit-funded support services.
- Set quarterly OKRs for non-dilutive funding sourced and public-sector revenue mix.
- Put an internal moratorium on “Google-first” for funding searches. Train your team to use curated portals and phone-first outreach.
Why it matters now:
- Wage growth for 90% of the population has lagged living costs for decades. Your workforce feels it—and turnover is expensive.
- Volatility is structural. Diversifying revenue with government contracts and stabilizing employees with community resources is a hedge against shocks.
Takeaway 2: The Phone Is a Power Tool—Because People Are the Product
Lesko’s counterintuitive rule: “Don’t start with Google. Start with people.” The reason is simple. Public programs are plentiful, fragmented, and updated constantly. The bottleneck isn’t forms—it’s wayfinding. You won’t find the exact right keywords for your use case without burning time. But the humans who run these programs are already funded to help you navigate. They are your free guides.
This is not theory. It’s system design. You invest an hour dialing a directory and you compress weeks of guesswork into a single conversation with someone who has solved your exact problem 50 times this month.
Where executives should send their teams first:
- For employee and family stability (rent, childcare, utilities, healthcare, dental, transportation, training): visit findhelp.org, enter your zip code, and call providers A-to-Z. These are nonprofits already paid to help. They won’t ask for money and they know the local landscape.
- For small business advisory and capital navigation: go to sba.gov/local-assistance. You’ll find SBDCs, SCORE chapters, Women’s Business Centers, and Veterans Business Outreach Centers—all funded to help you identify grants, lending, and growth resources.
- For contracting revenue: apexaccelerators.us (Apex Accelerators). They help you register, get procurement-ready, find opportunities, and bid strategically—for free.
- For job-creation incentives, site development, and local growth capital: find your state and regional offices via EDA.gov (Economic Development Administration) and their directories. These economic development teams are chartered to help businesses grow and hire.
Executive playbook to operationalize “Phone-First”:
- Build a contact pipeline. Assign a business analyst to create a living directory of relevant program managers, procurement officers, and nonprofit navigators by geography and sector.
- Script for calls. Teach staff to ask: “What programs match [our situation]?” “What keywords do you use to describe this funding?” “Who else should I talk to?” “What’s the next deadline and typical award size?”
- Track velocity, not just outcomes. Measure calls made, meetings set, pre-qualification achieved, registrations completed, and proposals submitted. Wins follow motion.
- Close the loop. After a successful connection, record the actual terms, cycle times, and compliance requirements. This becomes institutional knowledge you reuse.
Common executive mistakes to avoid:
- Paying third parties thousands for registrations, boilerplate proposals, or “insider lists” you can obtain free through Apex Accelerators and SBA resource partners.
- Treating grants as the only prize. Contracts provide repeatable revenue and enterprise value; grants can be episodic and time-bounded.
- Delegating entirely to junior staff with no executive air cover. Program partners move faster when they see leadership commitment.
Takeaway 3: Lead With Love—Because Culture Multiplies Capital
When I asked Matthew what gets better with age, he didn’t say speed or IQ. He said love. It’s not the word most executives write into a strategic plan. But in practice, it’s a leadership technology: a way of showing up that reduces fear, unlocks collaboration, and supports people through uncertainty.
Why this matters in funding and growth:
- Employees under financial stress underperform and churn. Pair salary with support. Normalizing the use of community resources—without stigma—makes your organization more humane and more productive.
- Partners are people. Procurement officers, program managers, nonprofit navigators—they remember who is respectful, consistent, and prepared. Love, expressed as professional care and follow-through, accelerates your path to yes.
- Executive energy is contagious. Before a hard meeting, set intention: may everyone here find clarity and benefit. Call it prayer, mindfulness, or focus—optimism and composure improve outcomes.
Embed love into operating practices:
- Create an Employee Stability Toolkit. Publish a simple guide for staff with links to findhelp.org, local rental and utility assistance, childcare subsidies, transportation help, and workforce upskilling. Train HR and managers to make warm referrals without judgment.
- Start meetings with a 30-second intention. Align on purpose, not just agenda. You’ll feel the difference in difficult conversations.
- Build “grace into goals.” When a deliverable slips, ask first: “What’s happening in your world?” Then recalibrate with clarity and accountability. Compassion and standards can coexist.
Link love to performance:
- Track retention, absenteeism, and time-to-productivity before and after offering navigation help to employees. Many companies see measurable improvements when financial stress is addressed.
- Capture the impact of contracting revenue on cash flow consistency and hiring quality. Stable revenue enables better culture investments—which further improve performance.
What About Politics? Operate on the 1–3 Year Horizon
Executives often ask whether a shift in administration will “turn off the spigot.” Matthew’s perspective is experience-hardened: rhetoric moves faster than reality, and most changes play out over decades, not quarters. Critical programs are baked into local constituencies and bipartisan incentives—jobs, infrastructure, public health, innovation—making abrupt disappearance unlikely. In other words, your next 12–24 months of opportunity are intact. Execute.
Pragmatic guidance:
- Ignore the headlines; follow the notices of funding opportunity, procurement calendars, and program officer guidance.
- Build resilience by diversifying across federal, state, county, and municipal opportunities.
- Keep your compliance clean. Changing winds favor well-run recipients.
Culture, Capital, Continuity: Redefining Executive Excellence
If you lead a company in 2025, you’re leading through compounding complexity: labor constraints, cost pressure, uneven demand, and investor scrutiny. That’s real. But so is the opportunity to tap into the other 40% of the economy with intention—and to lead in a way that dignifies the people who make your business possible.
Matthew’s journey reminds us:
- There is always more help than we think—if we’re willing to ask the right people the right questions.
- The most valuable tool is not an AI prompt or a pitch deck; it’s a phone call to a human whose job is to help you succeed.
- Love—expressed as care, patience, and clarity—is not soft. It is a strategic amplifier. It multiplies the value of every dollar you secure and every contract you deliver.
Build Community Capital Ops into your operating system. Turn your phone into a competitive edge. Lead with love that scales.
And yes—put a question mark on your planning board. It’s there to remind you: What’s the non-dilutive path? Who’s already funded to help? What would this look like if it were easy? Start calling.
Listen to the full episode on C-Suite Radio: Disrupt & Innovate | C-Suite Network
Watch the episode: DI 118 Unlocking Government Funding with Matthew Lesko
This article was drafted with the assistance of an AI writing assistant (Abacus.AI’s ChatLLM Teams) and edited by Lisa L. Levy for accuracy, tone, and final content.
