#94 Nigel Shanahan: The 20-Year Journey From IBM Salesman to a £50M Tech Exit

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

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