Inside the Broker's Mind: How to Sell (or Buy) a Business the Right Way with Sherryn Deetlefs - Sam Penny | Business Coach for Owners & Investors

Inside the Broker's Mind: How to Sell (or Buy) a Business the Right Way with Sherryn Deetlefs

 

Built to Sell | Built to Buy — Podcast Companion

Inside the Broker’s Mind: How to Sell (or Buy) a Business the Right Way with Sherryn Deetlefs

By Sam Penny · · 15–20 min read

If you’re planning to sell your business (or buy one), the difference between an average outcome and an exceptional one usually comes down to preparation, fit, and the story you present to the market. In this episode, business broker and former multi-business founder Sherryn Deetlefs joins me to unpack what really drives successful deals — from valuation drivers and SOPs to deal structuring, culture, and confidence with lenders.

Watch the episode on YouTube or listen on your favourite podcast platform.

Why You Should Get an Appraisal Early

The most repeated advice from Sherryn is refreshingly simple: get an appraisal earlier than you think you need it. An appraisal gives you a reality check on market multiples in your industry today — not five years ago — and it highlights gaps that you can fix before buyers (and lenders) see them.

Action in the next 30 days: Book a no-obligation appraisal. Use the insights to define a 90-day clean-up plan across financials, SOPs, owner dependence, contracts, IP and your data room.

Owners who get in early can reframe the next quarter around valuation drivers rather than just profit. You’re not only improving the P&L; you’re increasing buyer confidence, which is what really moves the multiple.

The Emotional Side of Selling (and Why Your “Why” Matters)

Businesses are personal. Whether you’re facing founder fatigue, shifting life priorities, or regulatory change, your motivation for selling becomes part of the narrative buyers weigh up. One of the first questions buyers ask is blunt: “Why is the business for sale?”

“Sometimes you’ve been jumping hurdles for so long that you’re ready for a new adventure. Knowing that early helps shape the right exit.” — Sherryn Deetlefs

Be honest and strategic. If the business is strong and you’re simply ready for the next chapter, that’s credible — especially when paired with steady financials and solid handover support.

Fit vs Price: When Culture and Operations Beat Dollars

In people-centred industries (health, wellness, education), cultural and operational fit can outweigh the highest headline price. Sherryn has seen vendors pass on multiple offers because the buyer wasn’t the right steward for the team and brand.

Define your ideal buyer profile early: skills, accreditations, leadership style, and growth approach. Then market to that profile. The right match shortens diligence, eases transition risk, and sustains performance post-handover — all factors lenders quietly love.

What Buyers Actually Value Beyond Revenue

Revenue and EBITDA are table stakes. Confidence in the future is what commands a premium. Boost it with:

  • Recurring revenue and retention (subscriptions, programs, contracts)
  • Documented SOPs for core functions and risk controls
  • Owner independence (a business that runs without you)
  • Brand & IP strength (differentiation that’s hard to copy)
  • Customer database quality (clean, engaged, permissioned)
  • Compliance readiness in regulated sectors

Think of your P&L as the past; your systems, brand and customer base are the future. Buyers price the future.

The Most Common (and Costly) Seller Mistakes

  1. Waiting too long to prepare. A rushed exit is a discounted exit.
  2. Tax-minimised financials without clear normalisations. Fine for the ATO, hard for lenders.
  3. No SOPs. Tribal knowledge kills buyer confidence and transitions.
  4. Owner-centric operations. If you’re the glue, the buyer prices that risk.
  5. Data room chaos. Missing contracts, murky IP, and loose licencing all slow or kill deals.
Pro tip: Ask your accountant to prepare a banker-friendly, normalised EBITDA pack with clearly labelled add-backs and a succinct rationale for each.

Deal Structuring That Saves Good Deals

Great buyers sometimes hit lending ceilings. Smart deal structuring can bridge the gap: staged settlements, vendor finance, leases on freehold with a timed purchase option, performance-based earn-outs, or asset splits. The goal is the same — de-risk cash flow for the buyer and keep the vendor whole on value.

If your broker actively networks with lenders, you gain realistic feedback early, reducing broken deals and wasted time.

A Practical Process for Buyers

Sherryn’s buyer workflow keeps momentum while protecting vendor confidentiality:

  • Confidential listing → EOI + NDA
  • Discovery call to test skills, motivation, capacity, and geography
  • Issue the Information Memorandum (IM): history, team, operations, financials, risks
  • Financing and fit checks, then a broker-hosted vendor meeting
  • Guided site walk-through (when appropriate), diligence list, and negotiation

Buying a business is more nuanced than buying a house. The question isn’t just “Can I afford it?” but “Can I operate and grow it?”

Red Flags for Buyers During Due Diligence

  • Excessive add-backs doing heavy lifting to reach valuation
  • Unclear licences/accreditations in regulated industries
  • No documented processes, or key-person concentration risk
  • Lease constraints (limited parking, restrictive covenants, short tenures)
  • Customer concentration or short-term contracts mislabelled as recurring revenue

A good broker will surface these early and encourage realistic mitigations rather than cosmetic gloss.

Why a Broker Who’s Been an Owner Changes the Game

Sherryn’s edge comes from building and exiting her own businesses. That background brings empathy and practicality: she knows handover quality matters, teams need stability, and that clean presentation plus accurate numbers make everyone’s life easier — including the banker’s.

How Storytelling Helps Sell Your Business

Numbers open the door; story closes the deal. Your IM should make it easy for buyers to “see themselves” running and growing the business:

  • Origin story: why the business exists and who it serves best
  • Unique value: what competitors can’t easily copy
  • Milestones: traction, retention, margin progress, quality metrics
  • Growth map: realistic levers for the next owner to pull
“Make the business shiny — not just to get through diligence, but to hand it over so the legacy actually flourishes.” — Sherryn Deetlefs

Quick Tips for Sellers

  • Get an appraisal now. Use it to plan a 90-day valuation sprint.
  • Separate personal from business expenses. Cleaner numbers = easier lending.
  • Systemise. Document SOPs for sales, ops, finance, compliance, and handover.
  • Build owner independence. Train your #2. Reduce single-point failure risk.
  • Prepare a banker pack. Normalised EBITDA, add-back schedule, contract summaries.
  • Define your ideal buyer profile. Then market directly to that fit.

Quick Tips for Buyers

  • Clarify your “why”. Income replacement, platform roll-up, or strategic bolt-on?
  • Get finance feedback early. Don’t fall in love before credit gives a path.
  • Prioritise stable revenue and retention. Then validate unit economics.
  • Assess cultural and operational fit. Can you lead this team on day 1?
  • Do disciplined diligence. Lease, licences, liabilities, and legal exposure.

Connect with Sherryn Deetlefs

If you’d like to learn more from Sherryn or get in touch about buying or selling a business, here’s where you can find her online:

Listen & Watch

Dive deeper into the full conversation with Sherryn, including real-world deal war stories and the exact questions she asks both vendors and buyers.


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Keywords: how to sell a business, business broker tips, buying a business, selling your business, business exit strategy, preparing your business for sale, business valuation tips, business acquisition strategy, business sale preparation, due diligence checklist

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