Their story starts on Ironside Road in nearby Huyton, famous now for being home to the Gerrard family, but where Culshaw’s grandparents also resided.
Their grandfathers were friends, their fathers were friends and, thanks to the latter duo uniting to coach Denburn Juniors, so too were young Tom and Steven.
And by the time they attended Cardinal Heenan High School together, it became clear that the boys enjoyed a mutual aptitude for football.
Culshaw saw his talents recognised with a call-up to represent England Schoolboys, while both players were soon snapped up by Liverpool’s youth setup.
And they subsequently moved through the ranks together, overcoming every hurdle to ultimately earn professional contracts with the club they loved.
Speaking to Liverpoolfc.com at the Academy, Culshaw, now Gerrard’s assistant manager with the club’s U18s, recalls those beginnings: “Steve Heighway, Dave Shannon and Hughie McAuley were my youth team [coaches].
“Then when I progressed to the Reserves where Sammy Lee was my coach, he made me captain, and I was around Ronnie Moran, Roy Evans, and all the old-school Boot Room staff.
“I’d progressed and everything went well for me. The national school, playing for England, joining Liverpool, signing professional at 17, progressing to the Reserves, captaining the Reserves.
“Then I was a pro for four years. It was a great time at Melwood because everyone was on the same site. I was training with Jamie Redknapp, Robbie Fowler, and Steve McManaman and learned an awful lot from them.”
It was at this point, however, that their paths diverged.
At a time when Gerrard was taking the first steps in what would eventually be regarded as one of the great Anfield careers, his good friend found himself out of contract and, for a period, trying out a new career.
Culshaw explains: “When I left I found it tough going on trials for lower league clubs. I got offered a couple of contracts at League Two clubs and I decided to knock them back thinking I could do a bit better.
“But when I started to go for trials it was taking longer and longer and then eventually I just fell out of love with the game.
“My friend had a tarmacking firm, so I went and worked with all my mates for a while.
“It was hard, it was a tough few years for me. Especially when I saw my mates, the likes of Steven, Carra, Michael Owen - lads who I’d come through the youth team with - progressing.
“I probably had my first bump in the road at 21 and I just really didn’t know to handle it.”
It took a number of years and a move abroad for Culshaw to eventually rediscover his love for the game - an epiphany prompted when he began coaching young children in Spain.
A return to Liverpool and studies in education followed, which led to work for the LFC Foundation College and a part-time role at the Academy that eventually turned full-time.
The opportunity to get back into football and to learn from some of the most well-regarded coaches in the country was not wasted upon a reinvigorated Culshaw.
He adds: “I was overjoyed to get the part-time role, just to be back involved with the club.
“To be working with a lot of talented youngsters, it doesn’t matter if you’re a part-time coach or full-time, you’re still working with the same type of boys all the time.
“I picked up loads and the club helped me work through my qualifications. When you go away you’re doing your B licence, your A licence, your youth modules, the club help you with that learning from the FA.
“But the main way of learning is on the pitches here at the Academy from top coaches.
“There’s a massive amount of knowledge among the coaches here and you’re just learning every day from them.”
This summer, Culshaw’s path and that of his lifelong friend Gerrard finally converged once more, the pair teaming up to take charge of the club’s U18s side.
They have overseen a strong start to life as a coaching unit - and the No.2 is understandably relishing every minute.
He enthuses: “I’ve loved it - working with the boys day-to-day and not just Steven but all the staff. We’re all still learning as staff, it’s really enjoyable.
“We’re only halfway through the U18s season and I just want to keep on progressing with the team until the end of the season. I’ve built myself up, starting off part-time, doing the U12s, U13s, U15s, now making the step up to the 18s.
“I’m just enjoying my role at the moment.”
In many ways, the two Huyton natives are the perfect coaching combination.
While Gerrard can share his experiences of competing at football’s very highest level, Culshaw offers a grounded insight into its harsher realities, and the importance of preparing for the possibility of life outside the game.
But just how much does that turbulent journey inform his coaching style?
Culshaw says: “It inspires me to be a coach, really.
“The lads I’m working with now, I’ve been through the journey that they’re on, I’ve made the next step.
“I played for the Reserves and trained with the first team on a daily basis, so I know what’s next, but I also know what’s next if they don’t make it.
“So I try and guide the lads in the right way.”
‘Behind the Badge’ is a regular feature on Liverpoolfc.com which aims to tell the individual stories of the numerous men and women who work tirelessly away from the spotlight in an attempt to make Liverpool FC successful.
We speak to various members of staff across the first-team, Academy and Ladies set-ups who dedicate their lives to the club each and every day, covering a variety of different roles that make a vital contribution in preparing the Reds for action.