Customers too risk-averse, class boundaries still endemic (it is amazing the US tech companies went into this, Google/Facebook/etc. seem to have hired the Notting Hill set as soon as they came to London), companies too conservative about investing margin in sales, very relationship-driven sales culture (as opposed to product-driven) that is closed to "outsiders", reluctance to cold-call, etc.
It is cultural because it can be anything else, do people from the UK have a different biology? No. I think if you look at politics in the UK, it is self-evident that the culture of the UK is not exactly entrepreneurial...unless you believe that a group of probably 30-50 people who went to the same school, went to the same university and largely studied the same course should rule the country...it is very weird.
In the UK, the working class used to be propelled upwards by grammar schools, [1] which selected children based on academic ability. Of course, there are problems around not wanting children who didn't get into grammar schools to be written-off, but I can't ignore their effectiveness in this regard.
The playing field can never be level. Where I am the grammar schools are as good as the private schools, but they are only in places where property prices are prohibitively high (ofc)...but they are the only effective way out (Sajid Javid went to a comp, it is possible but it is very rare and requires support from family that isn't available in most of the UK). The way to move forward is to aggressively stream students (not necessarily by ability, I went to a school with a guy who was thick as pig shit but went into St. Andrews because he worked hard, took his A-levels three times iirc), improve teaching, and offer more opportunities in poor areas (maybe even through positive discrimination, i.e. offer kids from poor areas a chance in a decent school...the UK used to have state-funded places in private schools).
You are right though, it isn't only cultural. Part of the reason why this group is so far ahead is their education system is far better.
My impression is that the UK and US are fairly similar in this respect. The leadership of the political and administrative class in both countries is dominated by graduates of a small number of institutions who took similar courses. In the UK it's primarily Oxford and Cambridge, and in the US it's Harvard, Yale and some other Ivy League colleges. There is a analogous pattern in many other countries.
Below is a list of all the national elections contested in the US and UK in the postwar period, noting the subject or subjects studied by the two leading candidates for head of government, along with the higher education institutions they attended:
USA
2020 Biden (Delaware/Syracuse, Law) v. Trump (Wharton, Economics)
2016 Trump (Wharton, Economics) v. H. Clinton (Wellesley/Yale, Politics/Law)
2012 Obama (Columbia/Harvard, Politics/Law) v. Romney (Brigham Young/Harvard, English/Law)
2008 Obama (Columbia/Harvard, Politics/Law) v. McCain (US Naval Academy)
2004 G. W. Bush (Yale/Harvard, History/Business) v. Kerry (Yale/Boston, Politics/Law)
2000 G. W. Bush (Yale/Harvard, History/Business) v. Gore (Harvard, Government)
1996 B. Clinton (Georgetown/Oxford/Yale, Foreign Service/PPE/Law) v. Dole (Washburn, Law)
1992 B. Clinton (Georgetown/Oxford/Yale, Foreign Service/PPE/Law) v. G. H. W. Bush (Yale, Economics)
1988 G. H. W. Bush (Yale, Economics) v. Dukakis (Swarthmore/Harvard, Politics/Law)
1984 Reagan (Eureka, Economics) v. Mondale (Minnesota, Politics)
1980 Reagan (Eureka, Economics) v. Carter (US Naval Academy)
1976 Carter (US Naval Academy) v. Ford (Michigan/Yale, Economics/Law)
1972 Nixon (Whittier/Duke, History/Law) v. McGovern (Dakota Wesleyan/Northwestern, History)
1968 Nixon (Whittier/Duke, History/Law) v. Humphrey (Minnesota/Louisiana State, Politics)
1964 Johnson (Texas State/Georgetown, Politics/Law) v. Goldwater (None)
1960 Kennedy (Harvard, Government) v. Nixon (Whittier/Duke, History/Law)
1956 Eisenhower (West Point) v. Stevenson (Princeton/Harvard/Northwestern, History/Law)
1952 Eisenhower (West Point) v. Stevenson (Princeton/Harvard/Northwestern, History/Law)
1948 Truman (None) v. Dewey (Michigan/Columbia, Law)
UK
2019 Johnson (Oxford, Classics) v. Corbyn (None)
2017 May (Oxford, Geography) v. Corbyn (None)
2015 Cameron (Oxford, PPE) v. Miliband (Oxford/LSE, PPE/Economics)
2010 Cameron (Oxford, PPE) v. Brown (Edinburgh, History)
2005 Blair (Oxford, Law) v. Howard (Cambridge, Law)
2001 Blair (Oxford, Law) v. Hague (Oxford, PPE)
1997 Blair (Oxford, Law) v. Major (None)
1992 Major (None) v. Kinnock (Cardiff, Industrial Relations)
1987 Thatcher (Oxford, Chemistry) v. Kinnock (Cardiff, Industrial Relations)
1983 Thatcher (Oxford, Chemistry) v. Foot (Oxford, PPE)
1979 Thatcher (Oxford, Chemistry) v. Callaghan (None)
1974 Wilson (Oxford, PPE) v. Heath (Oxford, PPE)
1974 Heath (Oxford, PPE) v. Wilson (Oxford, PPE)
1970 Heath (Oxford, PPE) v. Wilson (Oxford, PPE)
1966 Wilson (Oxford, PPE) v. Heath (Oxford, PPE)
1964 Wilson (Oxford, PPE) v. Douglas Home (Oxford, History)
1959 Macmillan (Oxford, Classics) v. Gaitskell (Oxford, PPE)
1955 Eden (Oxford, Oriental Languages) v. Attlee (Oxford, History)
1951 Churchill (Sandhurst) v. Attlee (Oxford, History)
1950 Attlee (Oxford, History) v. Churchill (Sandhurst)
1945 Attlee (Oxford, History) v. Churchill (Sandhurst)
Sandhurst is essentially equivalent to West Point. What is particularly notable about the UK is the number of Prime Ministers who were educated at Oxford: in the postwar period, all but two graduated from one of Oxford's various colleges. This probably has more to do with Oxford than the UK as a whole: in terms of prestige, academic success and establishment influence, Oxford and Cambridge are more or less identical, yet Cambridge clearly has a problem with producing Prime Ministers.
The US has a little more diversity in the academic institutions that educate its presidents, but that perhaps isn't surprising given it has about five times the population and about forty times the geographic area. A small number of institutions still dominate.
There is a little less diversity in the US in terms of the courses taken: all but three postwar US presidents have been law, politics, economics or history graduates. Of those who weren't, two were graduates of national armed forces academies, and one (Truman) had no degree. On the UK side there are graduates in chemistry, geography and languages, but law, politics, economics and history still dominate just as they do in the US (classics — which Johnson and Macmillan studied — is a combination of ancient history, languages (Greek and Latin), literature and philosophy).
Also, as I was careful to mention, the issue isn't necessarily that PMs went to the same university (although they did, your reasoning is backwards about Oxbridge...the UK has a large number of other very good universities that are better than Oxbridge in some subjects, the perception that it is a cut above is because all the PMs went there not because it actually is). It is cultural, and it is throughout govt...so in the US, you still see the same elite representation in the civil service...but it is nothing like the UK where there is close to 100% representation (the FCO is notorious for this, you need the right university, right high school, right primary education, and right parents...I know a guy who went to a £30k/year private school, parents went to Oxbridge, he got a first in IR from St. Andrew's a top university for IR, then got a distinction at KCL for IR again a top university globally for the subject, 4 high A grades at A-level...didn't even get an interview with the FCO). This is often very subtle because you have private schools teaching subjects like Classics...these subjects aren't really taught at all outside private schools, so if you go to a private school you can get into Oxbridge even if you are a relatively mediocre student if you apply to this subject (Theology is another, Land Economy is another...most students in the UK have no idea these routes into Oxbridge exist).
Oxford is top of the league and attracts brilliant, ambitious people so it's not surprising that it is over-represented at the top as well, though it's interesting that it dominates so absolutely. It may partly be self-reinforcing because I suspect that ambitious young people who want a career in politics think "right, first step is Oxford PPE".
In EU gambling and casinos are legal almost everywhere. There's no need to go to Vegas or make high risk investments.