Nobody is comparing him to Ole. He is a fantastic manager, no doubt, but he has never proved himself at a club with limited resources, or even resources the likes of a very big club such as Liverpool have. That is a fact you can't argue.
At Barca Pep inherited some of the best young talent in Spanish football history at the time that luckily happened to be there, he also happened to have the best footballer of possibly all time there. Not exactly Porto or Mainz.
He then inherited a treble winning Bayern Munich side who's job it is to walk the league almost every season, a shit ton of money but he still failed to win anything in Europe or do anything better than his predecessor or managers that would come after him.
Then he spent the odd billion pound at City managed through financial doping.
I made a list of all the League winning managers in the Top 5 Leagues since 2000 and it was interesting to note who worked their way up and who were born with a silver spoon.
Ottmar Hitzfeld - Did well in Switzerland, won Leagues and a European Cup with Dortmund and then made his way up to Bayern where he enjoyed even more success.
Carlo Ancelotti - Started his management career at Reggiana, then to Parma, Juventus - did well overall and then to Milan where his successes took shape. His win percentage kept increasing as he took over clubs with more money like Chelsea, PSG, Real Madrid and Bayern.
Louis van Gaal - Started at Ajax, which is a masive help, but apart from League titles, he won the European Cup with Ajax as well, which showed his mettle. Then moved to Barcelona, was successful, but one of his biggest successes would be to win the League with AZ Alkmaar, when the decade was largely dominated by PSV and Ajax. Then moved to Bayern to continue his success, did decently with the Dutch national team and then fizzled away at Man United.
Jupp Heynckes - Started his management career at Mönchengladbach, was successful, moved to Bayern, won Leagues, then moved to a few other clubs like Bilbao, Frankfurt and Tenerife, did well overall, earned a move to Real Madrid, won the European Cup, had stints at Benfica, Bilbao and Schalke and then went back to Bayern, winning Leagues and the Champions League.
Jürgen Klopp - Worked his way up starting from Mainz, earning promotion and doing very well, moving to Dortmund, winning Leagues and almost winning the Champions League, moved to Liverpool, won the League and the Champions League.
Hansi Flick - Started by managing a non League side, then moved to Hoffenheim, where he was hugely successful, earned a move to Bayern, won Leagues and the Champions League and is now the manager of German National team.
Felix Magath - Started his career with the reserve side of Hamburg, worked through a bunch of teams and then had a successful spell at Stuttgart that earned him a move to Bayern, where he won the League twice. The highlight of his career was when he won the Bundesliga with Wolfsburg in his next stint. He did well at Schalke before he fizzled out.
José Mourinho - Started at Benfica, and then made a big impression at Porto, winning both the UEFA Cup and the Champions League, moved to Chelsea, won Leagues, moved to Inter, won Leagues and the Champions League, did well at Real Madrid and return stint to Chelsea intially, before fizzling out.
Marcello Lippi - Started in Serie-B with Pistoiese, worked with a bunch of clubs, worked his way up, got the Napoli job, and then immediately got the Juve job where he was hugely successful. He won 5 League Titles and a Champions League, was runner-up thrice. Then managed Italy, won the World Cup and then fizzled out eventually.
Fabio Capello - Started at Milan after Sacchi, looks like he was handed it on the platter, won 4 Leagues and a Champions League, won the League at Real Madrid, but also went to Roma and won the League for them, which is probably his biggest achievement. Fizzled out after a successful return to Real Madrid, after the Juventus debacle.
Roberto Mancini - Started at Fiorentina, won a Cup with them, as he did with Lazio, then moved to Inter, where he won 3 Leagues, moved to Man City where he won the League once, and then won the Euros as the manager of Italian National team.
Massimiliano Allegri - Started with Aglianese in Serie-D, moved to several clubs, before winning the League with Milan, right at the start of their difficult period, and then earned a move to Juventus, where he won a further 5 Leagues.
Antonio Conte - Started at Serie -D, worked his way upto Serie-A, won 3 Leagues with Juventus, moved to Chelsea, won a League with them, then moved to Inter to win the League with them and break the Juventus monopoly.
Alex Ferguson - Started in the Lower tiers of Scotland, before being successful with Aberdeen and eventually moving to Man United where he won 13 Leagues and 2 Champions Leagues.
Arsène Wenger - Started as manager of Nancy, worked his way up to Monaco, where he did well and won the League, then moved to Japan and then came to Arsenal where he won 3 Leagues and was successful.
Vicente del Bosque - Kind of handed in a platter after working for Real Madrid academy, was successful with Real Madrid and the Spain National team, albeit with their Golden generation and some of the best players ever.
Zinedine Zidane - Similar to del Bosque, moved from the academy to Real Madrid to win 2 Leagues and 3 Champions Leagues.
Rafael Benítez - Started with Real Madrid reserves, but had to move to Valladolid, switched to several clubs, before finally landing at Valencia, where he was hugely successful in winning 2 League Titles and a UEFA Cup. Then moved to Liverpool, won the Champions League, moved to Chelsea and won the Europa League, won the Cup with Napoli, had a good stint with Newcastle, before fizzling out.
Diego Simeone - Started with Racing Club, worked through a number of clubs before landing at Atletico, with a successful stint of winning 2 Leagues, 2 Europa Leagues and reaching the Champions League finals twice.
Luis Enrique - Started with Barcelona reserves, moved to Roma, did okay and then to Celta before being successful with Barcelona winning 2 Leagues and a Champions League before taking up the Spain National team job.
Thomas Tuchel - Started with Augsburg reserves, did well at Mainz and Dortmund, landed the PSG job, won two Leagues, moved to Chelsea and won the Champions League.
Gérard Houllier - Started at amateur French club, won the League with PSG, took up Technical director roles, took over a struggling Liverpool, won the Europa League and two Cups, won two more Leagues with Lyon.
Most of these managers worked their way up from lower ranked clubs, some of them from lower leagues before reaching their successes. Guardiola is one of the few like del Bosque and Zidane to have started with the richest/one of the most successful clubs in their Top League with a Top class squad to choose from. As well as he has done, he is yet to prove that he can work his way up and still be successful.
I think more credit should be shown towards many of the above successful managers who have worked their way up from below, rather than just counting trophies that were won. Winning the League with Stuttgart, Wolfsburg, Dortmund, Roma, Atletico, Valencia, Liverpool (against current Man City), Leicester, AZ Alkmaar, or Lille (against current PSG), winning the Champions League with Dortmund, Porto are extraordinary achievements and are not equal to the routine League titles won by a few others. A few others did extremely well before earning moves to the big clubs as well.
Guardiola took over a Barcelona side that did the Double of League Title and Champions League just 2 years before. He took over Bayern who had just won the treble including the League Title and Champions League and still failed to win the Champions League in 3 years. Man City were winning League Titles before he was appointed. He's yet to win the Champions League with them. Yes, he made these teams stronger in their Leagues, but all of those three clubs were some of the richest clubs not in their Leagues, but in the whole world at the time of his appointment, not to mention, hugely successful as well. This has to be taken into context when we rate managers overall.