Deals Down Under

Dimitri Nikolakakis

Deals Down Under is the podcast for aspiring and active acquisition entrepreneurs in Australia. Each episode, host Dimitri Nikolakakis sits down with founders, operators, and dealmakers who have bought, built, and scaled businesses the unconventional way — without starting from scratch. From first acquisition to complex roll-ups, we dig into the mechanics of deals, the realities of ownership, and what it actually takes to buy your way into business in Australia. If you're tired of startup culture and ready to build wealth through acquisition, this is the show for you. Your Host: Dimitri Nikolakakis is an entrepreneur based between Cape Town and Melbourne, with a background spanning digital marketing, business acquisitions, and deal structuring. After building and scaling a performance marketing agency, Dimitri pivoted to acquisition entrepreneurship — aiming to buy, structuring, and operate businesses rather than building them from zero. He has spent the past several years working on a roll-up and acquisitions in Africa. Deals Down Under is his effort to document and better understand the Australian acquisition landscape — a market full of opportunity that remains almost entirely undocumented — and to build the community of operators and dealmakers that should exist around it.

Episodes

  1. 1 day ago

    Give Me 40 Minutes and I'll Explain How to Buy a Business With a Search Fund | Jackson Allan

    If you have bought a business, and are open to sharing your story on the show, please email ddu.dimitri@gmail.com If you want to sell your business, I'm buying. Please email ddu.dimitri@gmail.com Connect with Jackson Allan here: https://www.linkedin.com/in/jacksonallan1/ Most people assume you need to be rich, or technical, or both, to buy a business. Jackson Allan is neither. After 15+ years in B2B commercial leadership across Australia and the US, he founded the search fund Touchstone Point in 2024 and — 30 days before this conversation — closed on Passmark Software, a 27-year-old company built by a computer scientist that operates at the deep technical interface of hardware and software, with customers like Apple, Boeing and Milwaukee Tools. There's a nice symmetry to it: the deal traces right back to his own roots rebuilding computers as a kid. He did it through the search fund model — raising capital from investors first, then hunting for the right business to step into as CEO, without signing a personal guarantee or putting his own assets on the line. In this episode Jackson pulls back the curtain on the entire search fund model — where it came from, why a first-time buyer would choose it over going it alone, and exactly how the economics work for the searcher (the salary haircut during the hunt, the equity upside after). He's refreshingly concrete about the grind: 2,500 cold outreaches narrowed to 400 replies, 100 conversations, 20 serious looks, and one deal. He breaks down staging due diligence on a cross-border, multi-jurisdictional deal to limit broken-deal costs, the very real "deal fatigue" that sets in after six months, and what the chaotic first 30 days of ownership actually involve. If you're an operator drawn to acquisition but stuck on "I don't have the capital" or "I'm not technical enough," this is the operator-to-operator playbook for a path most people in Australia and NZ have never heard of. (Note: the deal is under NDA, so Jackson keeps specific figures off the table — the value here is the model and the process.) TIMESTAMPS: 00:00 — Intro / thank-you 00:18 — First 30 days and early context 01:59 — Sales background and how it started 03:54 — What Passmark does 07:48 — How you got here from sales 14:09 — Search fund model and investor conversations 23:44 — Founding the business 26:47 — Deal process and due diligence 30:26 — Completing the deal and reflections 32:01 — Looking back after making it through the process Deals Down Under is the podcast about buying, selling, and growing businesses in Australia and New Zealand. Subscribe wherever you listen to podcasts.

    36 min
  2. 17 June

    The Lazy Entrepreneur's Way to Buy 3 Businesses FAST! | Elisha Nuttall

    If you have bought a business, and are open to sharing your story on the show, please email ddu.dimitri@gmail.comIf you want to sell your business, I’m buying. Please email ddu.dimitri@gmail.com Connect with Elisha here: https://www.linkedin.com/in/elishanuttall/ After ten years writing reports at PwC and Grant Thornton telling other people how to fix their businesses — and watching them do nothing with the advice — Elisha Nuttall decided to take his own. In 2022 he and a long-time friend bought their first company, a hand-built aerial manufacturer that was being run on paper. Three deals later, Talanton Holdings owns a group doing around $4M in revenue and over $2M EBITDA, and Elisha is involved in the first two businesses for about half an hour a week. Elisha breaks down every deal with real numbers: the multiples he paid, how he stacked vendor finance against bank debt, why he deliberately offered $100K over asking to win 0% vendor finance, and how he funded two more deals on internal equity and a bit of family money while keeping control tight. If you've ever wondered whether you can actually buy a business and step back to do it again (instead of buying yourself a 80-hour-a-week job), this is the operator-to-operator conversation that shows how the management-team-first model really works. IN THIS EPISODE: Why turning up sweaty and bleeding to the first seller meeting actually won the dealThe exact capital stack: 30% equity, vendor finance and bank debt split across the other 70%Why he paid $100K over asking — and got 0% interest for 2.5 years in returnThe brutal trade-off: not paying himself for two years to pay down debt fasterTurning a paper-run, no-systems manufacturer into a quality leader in 12 monthsThe three-tier reporting structure that lets him run multiple businesses remotelyHow he de-risked a family business (husband, wife and daughter all in senior roles)Surviving COVID, container-rate spikes and supply-chain chaos through every dealTIMESTAMPS: 0:00 - The first deal: a paper-run aerial manufacturer 0:15 - Showing up sweaty and bleeding (and why it worked) 2:32 - The numbers: revenue, EBITDA and a 3.5x multiple 4:00 - Building the capital stack: equity, vendor finance, bank debt 5:12 - "I didn't pay myself for the first couple of years" 5:53 - Why he offered $100K over asking price 8:00 - Who is Elisha? From PwC and Grant Thornton to acquisitions 12:31 - The childcare deal that fell apart at the last step 13:04 - Day one of ownership: a hundred little decisions 16:24 - The big levers: foundations, quality and QA test sheets 22:59 - How a non-engineer ran a manufacturing turnaround 25:15 - Building a management team through promotions 28:40 - Can you really step away? Half an hour a week 30:25 - Keeping customers happy without the owner in the room 40:15 - Funding deal two with vendor finance and family equity 41:10 - Deal two: a 60-year-old powder-coating business 41:19 - Deal three: Signals NZ and the family-business red flag 44:20 - Writing the daughter into the contract 48:04 - The silent partner: his CFO with a day job 49:41 - "Any oh-shit moments?" COVID, shipping and war 50:33 - The lifestyle: $4M of businesses, ~30-hour weeks 54:31 - Headline numbers and what he bought vs. what it's worth now

    46 min
  3. 10 June

    Two Off-Market Acquisitions, Two Completely Different Seller Experiences | Matt Stevenson

    Matt Stevenson started his career in Big Four M&A before moving into banking — watching businesses fail not because they were bad, but because their owners couldn't manage them. That became his thesis for buying his own. He's now Managing Director of Bizstats, a monopoly SME sales data provider, and NZ BizBuySell, New Zealand's leading business-for-sale platform — both acquired off-market from sellers who weren't looking to sell. The two deals couldn't be more different. Bizstats came from a deceased founder's children who had no idea what the business did; Matt fired the operator after one week. NZ BizBuySell was chalk and cheese — a founder who stayed on, taught him everything, and genuinely wanted him to succeed. In this episode Matt gets honest about twelve months of persistence on two separate proprietary deals, how he funded them, why vendor trust beats any financial metric, and why most people in ETA over-analyse everything and never actually buy anything. IN THIS EPISODE: The year-long search for Bizstats — and why the sellers' ignorance of their own business was the biggest riskHow he transformed a Microsoft Access-era business into an automated platform and grew revenue 50%Why he fired the operator after one week — and ran the business alone at 4:30am before his day jobWhy vendor trust is his #1 green flag — above anything in the financialsHow COVID house prices unlocked his first acquisition — and why funding is the real bottleneck for most buyers in their 30sWhy he took vendor finance on the second deal even though he didn't need itAdvice to his younger self: partner up, buy bigger, move faster CONNECT WITH MATT: LinkedIn: https://www.linkedin.com/in/matt-stevenson-53208493 TIMESTAMPS: 0:00 - Matt's path from Big Four M&A to business ownership 2:55 - Discovering Bizstats: data gold behind a 70-year-old's inbox 4:24 - Settlement date vs. C-section date 4:57 - What Bizstats is and why it was worth buying 7:17 - Multiple and deal structure for Bizstats 8:18 - Proprietary search: wearing a seller down over 12 months 10:06 - Funding the deal: COVID house equity, cash, and bank debt 11:51 - Transforming Bizstats: from Microsoft Access to automated SaaS 14:18 - How AI changed the economics of small business tech 15:38 - Discovering ETA after already doing ETA 18:00 - Finding NZ BizBuySell the same way he found Bizstats 19:31 - Comparing the two deals: size, staff, sophistication 20:28 - Deal structure for NZ BizBuySell 22:16 - Going full time: the first Christmas break he didn't dread 23:20 - Crap moments: misrepresentations and firing the operator 25:37 - Owner trust: the #1 green flag in any acquisition 26:23 - Vendor finance as post-settlement protection 27:13 - How the NZ BizBuySell deal was funded 29:02 - Monopoly positions and why they made both deals easier to back 30:08 - On over-analysers in ETA who never buy anything 31:44 - Synergies between Bizstats and NZ BizBuySell 33:07 - What comes next 34:53 - Advice to younger self: partner up, buy bigger, move faster Deals Down Under is the podcast about buying, selling, and growing businesses in Australia. Subscribe wherever you listen to podcasts.

    34 min
  4. 3 June

    From Operator to Investor: How Pete Seligman Built a Portfolio of 10+ Acquisitions

    Pete Seligman has been buying, running, and backing businesses since 2013. He started the way most acquisition entrepreneurs do - a mate, some savings, and a bank loan secured against their houses. Today, as the founder of EtA Forum and EtA Central, he's Australia's most active Search Fund investor, directly involved in 15-20 deals and having backed more than 20 searchers across the Asia-Pacific. In this episode Pete gets honest about what it actually takes to build a portfolio of small businesses. There's no ten-step framework and no passive income shortcut - just hard-won lessons on delegation, deal structure, earn-out negotiation, and the mental discipline required to show up for ten different businesses without losing your mind. IN THIS EPISODE: How Pete manages board positions across 10+ companies (and the Bill Clinton trick he uses to stay focused)Why you should never assume you can just "install a CEO and walk away"Why delegation - not deal-finding - is the real reason most small businesses never break through the $20-30M revenue ceilingHow Search Fund deals are structured: equity splits, vesting, and IRR hurdles explained plainlyFunding options for solo acquirers in Australia without a Search FundHow Australian sellers really feel about earnouts, including a seller who turned down a free $1MWhether keeping the seller involved post-close actually works CONNECT WITH PETE: Website: www.peteseligman.com.au LinkedIn: https://www.linkedin.com/in/peteseligman YouTube: https://www.youtube.com/@PeteSeligman TikTok: https://www.tiktok.com/@peteseligman TIMESTAMPS: 0:00 - Managing multiple businesses: plate spinning vs juggling 2:52 - The Bill Clinton brain compartmentalisation trick 6:46 - The myth of "buy a business, drop in a CEO, walk away" 10:16 - Delegation: the #1 ceiling for small business owners 13:55 - Running two businesses at once 15:52 - Pete's shift from operator to Search Fund investor 18:34 - How Search Fund deals are structured 21:46 - Funding an acquisition without a Search Fund in Australia 24:26 - Earnouts and vendor finance in Australia 27:58 - Should the seller stay on after the deal closes? Deals Down Under is the podcast about buying, selling, and growing businesses in Australia. Subscribe wherever you listen to podcasts.

    54 min

About

Deals Down Under is the podcast for aspiring and active acquisition entrepreneurs in Australia. Each episode, host Dimitri Nikolakakis sits down with founders, operators, and dealmakers who have bought, built, and scaled businesses the unconventional way — without starting from scratch. From first acquisition to complex roll-ups, we dig into the mechanics of deals, the realities of ownership, and what it actually takes to buy your way into business in Australia. If you're tired of startup culture and ready to build wealth through acquisition, this is the show for you. Your Host: Dimitri Nikolakakis is an entrepreneur based between Cape Town and Melbourne, with a background spanning digital marketing, business acquisitions, and deal structuring. After building and scaling a performance marketing agency, Dimitri pivoted to acquisition entrepreneurship — aiming to buy, structuring, and operate businesses rather than building them from zero. He has spent the past several years working on a roll-up and acquisitions in Africa. Deals Down Under is his effort to document and better understand the Australian acquisition landscape — a market full of opportunity that remains almost entirely undocumented — and to build the community of operators and dealmakers that should exist around it.

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