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Nigel Shanahan started his working life as a chartered accountancy trainee who "failed miserably", found his feet as an IBM salesman for 12 years, then left with a colleague and £250,000 of business angel funding to launch a text-messaging business at the start of the 2000s. It took another 20 years, one dilution to 5%, one buyback of his own company from the VCs, one moment of clarity at an M40 service station, and one 4:30am deal signing to build Rant and Rave into a business he sold to Upland Software in 2018 for what he'd told his team eight years earlier it would be worth: £50 million.

In this episode:

• Loughborough University, a failed 18 months as a chartered accountancy trainee, and how a graduate management programme at IBM turned him into a salesman for 12 years
• The Warwick University EU-funded programme (six Saturdays and Sundays in a row) that separated the entrepreneurs-in-waiting from those who'd stay in corporate life
• The mentor, Harry, who ran that programme, and who Nigel credits with being one of the most important business relationships of his career
• The first business idea: SMS broadcast for corporates in the days when only people with "status" at IBM had a phone in their car, and the £250,000 angel investment that landed six weeks after the first pitch
• The £100k+ IBM salary he walked away from, the £25,000 a year he paid himself for three years, and the young family who paid for it too
• The VC round that came next, the discipline it forced on him, and the phone call telling him his co-founder Ian had to go — and the "hardest business conversation" of Nigel's life the next morning
• Being diluted to 5%, working 80-hour weeks, having remortgaged the house five times, and the moment at the M40 Welcome Break service station where Rant and Rave was born
• The wife, Desi, who told him it was "bloody brilliant" before anyone else did
• Harry's response when Nigel said he'd walk away and start over: "Don't be ridiculous. Do an MBO"
• The Vodafone relationship changing at exactly the right moment, the board panicking, and the MBO that ended with the VCs getting every pound of their money back
• The sentiment engine that turned SMS broadcast into a two-way customer feedback business, and the ten further years of building that followed
• The £50 million valuation Nigel told the team was possible eight years before it happened, and the 64 staff on the Enterprise Investment Share Scheme who came along for the ride
• The wrong CEO hire that came from "meals and drinks" instead of a proper process, and the non-exec chairman Simon who asked the killer question over a curry: "what's the exit strategy?"
• Implementing the Entrepreneurial Operating System (EOS), the beauty pageant with investment banks, and picking GP Bullhound
• The 2.5x ARR multiple SaaS deals used to go for, the £20M annual recurring revenue that got them to their target price, and the twin-track PE vs trade sale campaign
• Why the senior team chose Upland Software over a leveraged private equity offer at the same valuation, and the 40-day due diligence that followed
• The 4:30am signing after Nigel "threw his dolly out" and demanded the acquiring CEO come back from a golf trip, and "Disco Dave" — the M&A lawyer from Northern Ireland who arrived three weeks before the deal after the original partner left the firm
• Life after the exit: Mill Street co-working in Leamington Spa, the Make Good Grow philanthropic matchmaking platform, and Nigel's definition of true wealth — "happiness and contentment"

A conversation about betting on a technology wave before anyone else can see it, why not all VCs are the same, and how a 20-year "overnight success" actually gets built.

This podcast is produced by Tribunista

Sponsored by Capital Partners

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Mark Mills started buying and selling at school — literally, with bags of broken biscuits from the biscuit factory where his aunt worked. Three decades and five businesses later, after a £20,000 debt from the failed pay phone venture that took years to clear, and a publishing business he sold for £1, he built Cardpoint into a £100M-a-year cash machine business turning over £2M a week. He now takes other founders through the 40-step process he ended up writing after selling his own company disastrously badly on the first attempt.

In this episode:

• The broken-biscuits business at school that started it all, and why he thinks the best entrepreneurs are always capable salespeople
• The pay phones business in the early '90s that made money on hardware but nothing on calls, and the recession that wiped it out
• The £20,000 debt he decided to pay off personally rather than take anyone down with him
• The mobile phone moment: sitting around a table laughing at the idea that "someone would want one for his wife" — and the revolution they completely missed
• The publishing business that got so broad it had no audience, and the £1 exit that followed
• The 1999 trip to New York with his brother "because all the good ideas come from the States"
• The five business model rules it took him three failed ventures to figure out: recurring income, location-independent, scalable, necessary rather than fashion, and of its time
• Cardpoint: 36,000 free ATMs already in the market, and the counter-intuitive decision to put paid ones in more convenient locations — corner shops, petrol stations, tourist spots
• The maths behind £1.50 charges adding up to £100M in revenue, and why the business ended up needing a lot of accountants
• Why he ran Cardpoint with an exit in mind from day one, and how that discipline shaped every small day-to-day decision
• The disastrous first attempt to sell it — running buyer meetings while trying to do his day job — and the Christmas Day conversation with his wife that reset everything
• The six-month "I'm not for sale" period he used to prepare properly, and why saying no created more interest not less
• The 40-step exit process he now takes founders through, from tidying up leases and share structures to sharpening the sales pipeline
• The four kinds of buyer he thinks about: PLCs, PE-backed roll-ups, private equity taking a hybrid stake, and pure trade sales — and the Minicam deal that used two of them
• Why buyer due diligence matters as much as the other way round, and the founders who took less money because they preferred one buyer's team to another's
• The anticlimactic feeling after selling — the founder who ate beans on toast and cried the night the deal closed, and Mark's advice to do nothing for 12 months afterwards
• Marking the occasion: daft cars, one burnt orange McLaren, and a pair of cufflinks Mark still wears years later
• The five "disinheritance events" his kids can recite, and why they occasionally try to talk each other into breaking the rules
• His definition of true wealth: not the money, but the choices — and why he'd rather be rich than famous

A conversation about ruthlessly interrogating your own business model, the discipline of running every day as if the exit is coming, and why the moment after the wire transfer clears is often quieter than anyone expects.

Mark's Website: https://www.mark.co.uk
Book “Making Your Mark” - https://amzn.eu/d/04iC0CF7

This podcast is produced by Tribunista

Sponsored by Capital Partners

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Niraj was 30, healthy and getting ready for work when a stroke put him on the bathroom floor and eventually into the stroke unit at St Mary's Hospital in London.

Fifteen years on, he has built five businesses across property, meditation, sports tech and now M&A, all while carrying two convictions the health scare gave him: that a useful thought beats a true one, and that energy is a strategy in its own right. His latest venture, DKZ Equity, is out to fix what he sees as broken about how smaller entrepreneurs get sold.

In this episode:

• The stroke at 30 that came with no family history, no warning and no explanation, and the "car crash" analogy his doctors used when they discharged him
• The father he lost at 14 to a heart attack aged 47, and the two ambitions that shaped Niraj at 15: run his own business and see the world
• Why the plan he was already forming to leave employed life got accelerated the day he woke up in hospital
• The year he spent inside two tech startups just to learn how to build, and the mistake he was making that stopped anything getting off the ground
• The pivot into real estate out of "desperation and frustration", the London Plan document nobody in property was reading, and the co-living niche that replaced his salary
• Why he built video viewings, electronic signatures and fibre-optic broadband into his lettings in 2012, and why he still finds property "incredibly boring"
• Riding the London wellness wave in 2014 and 2015, building a meditation and mental wellbeing movement, and the "moderately successful" exit that taught him more than a bigger one might have
• The sports tech partnership with Mac Lackey that nearly delivered a seven-figure exit on something that fundamentally didn't work
• The three near-miss accountancy acquisitions that turned into the origin story of DKZ Equity in December 2024
• Why he thinks the sub-£50M M&A market is where things get "murky", and the incentive structures that push good advisers up-market
• The retainer-free M&A model he thinks founders should be wary of, the four-to-six percent fee range, and the tail provisions that have quietly wrecked good deals
• The 24-month tail clause that trapped one founder, cost them a £20M exit and forced them into another funding round
• Why he stacked his firm with two experienced partners from day one, and why he almost never takes equity when early-stage founders offer it
• Energy as a strategy: the physical, mental and social edge that shows up in every meeting whether you notice it or not
• His two-part definition of true wealth: winning the demographic lottery of a free-market Western economy, then having the bravery to define what you actually want rather than what social media tells you you should

A conversation about treating your own health as infrastructure, building businesses in markets other people have written off, and the questions every founder should be asking before they sign an M&A engagement letter.

Niraj’s LinkedIn: https://www.linkedin.com/in/niraj5hah/

DKZ Equity Website: https://www.dkzequity.com

This podcast is produced by Tribunista

Sponsored by Capital Partners