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.
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