Hey, founder friends! If you’re running a $5 million to $50 million business, you’re in the sweet spot—big enough to matter, scrappy enough to hustle. But when it’s time to sell, grow, or snag some capital, investment banking can feel like a black-tie gala you weren’t invited to. Fear not—I’m Daniel, and at Icon Business Advisors, we’re out there meeting top entrepreneurs across the U.S., from tech rebels to manufacturing mavens, and helping them crack the investment banking code. No stiff suits or secret handshakes required—just solid best practices to get you from “what now?” to “we nailed it.” Let’s break it down with a little grit and a grin.

1. Know Your Worth (and Prove It)

First rule of investment banking club: don’t guess your value—know it cold. Founders often stroll in thinking their business is worth a gazillion bucks because they love it (and who wouldn’t?). But bankers want hard numbers—revenue, profit, growth trends. We’ve met entrepreneurs from Seattle to Savannah who learned this the hard way—vague vibes don’t cut it. Get your financials squeaky clean and build a story that pops. At Icon, we’ve turned messy ledgers into gold for founders, landing valuations that make jaws drop. Step one: shine up your worth like it’s date night.

2. Pick the Right Partner, Not Just the Flashiest

Investment bankers aren’t one-size-fits-all—choosing one’s like picking a dance partner, not a trophy. Big Wall Street firms might dazzle, but they’re often too busy chasing unicorns to care about

your $20 million gem. Boutique players or folks like us at Icon get the lower middle market—we live it. We’ve seen founders in Denver and Dallas ditch the glitzy names for partners who actually get their industry, whether it’s software or specialty retail. Ask: Do they know my world? Do they fight for me? The right fit beats a shiny logo every time.

3. Prep Like It’s Game Day

Investment banking’s not a “wing it” sport—prep is your superpower. Before you pitch buyers or investors, nail your homework: a killer pitch deck, a tight Confidential Information Memorandum (CIM), and answers to every “what if” they’ll throw at you. We’ve worked with founders in Chicago who thought charm would carry the day—spoiler: it didn’t. Buyers sniff out gaps faster than a hound on a trail. Our team’s drilled this with entrepreneurs nationwide—prep hard, and you’ll strut into the room like you own it (because you do).

4. Play the Long Game with Relationships

Deals don’t happen in a vacuum—relationships grease the wheels. Top investment bankers (and us at Icon) lean on networks—buyers, lenders, industry insiders—to make magic happen. We’ve met founders in Austin who skipped the schmoozing and regretted it—cold calls don’t close deals. Start early: chat up potential partners, join the conversation, build trust. Our 400+ boutique bank connections? That’s years of handshakes paying off. For founders, it’s not just a transaction—it’s a Rolodex that wins.

5. Leverage Tech Without Losing the Soul

Here’s a hot tip: tech’s your co-pilot, not your replacement. Modern investment banking’s buzzing with tools—AI for deal sourcing, data for valuations—and it’s a game-changer for the lower middle market. We’ve got Betty, our AI whiz, helping founders from Portland to Miami spot opportunities faster than you can say “due diligence.” But here’s the kicker: tech alone’s cold—pair it with human savvy. We’ve seen it work wonders—matching a Midwest maker with a buyer in days, not months. Use the gadgets, but keep the heart.

Why This Matters for Founders

Investment banking isn’t some ivory tower mystery—it’s your ticket to scaling, exiting, or cashing in, done right. We’re out there with top entrepreneurs, seeing founders turn sweat into success with these moves. A California techie doubled her sale price with prep; a Texas retailer snagged capital with the perfect partner. For you, it’s about owning the process—not getting lost in it. These best practices level the field, and they’re yours to grab.

How Icon’s Got Your Back

At Icon, we live this stuff—meeting founders across the U.S., we’ve built a playbook that’s less “corporate jargon” and more “let’s get it done.” We polish your value, match you with the right players, and blend tech with hustle to make deals sing. Whether you’re selling a $15 million operation or raising funds to grow, we’re your wingman—because founders deserve more than a handshake and a bill.

Ready to rock the investment banking game? Let’s chat—I’d love to hear your story and swap ideas. Hit me up at Icon—no fluff, just founder-to-founder talk. Because your business isn’t just numbers—it’s your legacy, and we’re here to make it a win.

Daniel Askew is the CEO of Icon Business Advisors, serving the real American Icons… our business leaders.