Novice - 330 miles, 2 days, 1 month to get fit. $600k wager if not. Doable?

I really dont think its an issue.

Theres a charity ride round here - its only 50 miles but people of all shapes and sizes do it on bikes that dont fit them and aren't suited and wearing jeans and god knows what.  

So he's time to prepare and he can get the right advice - and there's a lot of money to be won ? 

He should easily do it.  Slow and steady. 

With help from LA... I wonder whether the wager has any terms on doping? 

Huh, maybe he will have another heart attack after all. As he doesn't need the money, perhaps motivation is more of an issue than first thought. I'd still do it if you have a few bob to spare. 

Pfffft - playboys today. Lightweights.

Dan Bilzerian? The chap who had 2 heart attacks before the age of 30 from "5 days of partying, snowboarding, gambling, crazy sex, sleep deprivation, consumption of cocaine and the introduction 200 milligrams of Viagra*", survived being treated for said heart attacks by Michael Jackson's doctor; self-confessed gun nut and Trump supporter? That Dan Bilzerian?

If it were a flat 330 miles, he might have grounds to be optimistic. But the route's a bit lumpy, especially on the second day. About 4,000 metres of climbing, and possibly high temperatures. Will be... challenging.

* that sounds like a GC from the - cough - good old days.

An unfit rider would do well to average 12 mph over 160 miles/day. Biggest problem will be saddle sores and aches and pains in the rest of the body. Not to mention fueling/hydrating the ride each day. Is this a supported ride?

I'd think that would be pretty easy, a month is enough time to get the body used to a bike and used to putting in some serious saddle time.  A 600k wager is enough to know that it's going to be his primary focus and not something that is fitted in around a 9-5 job.

Depending on the terain, it's 8-10 hours on a bike for two days, less if he has other people ridding with him to split the work up.

For Six Hundred Thousand Dollars you could get just about anyone to do this unless they are super obese or dying of heart disease... [googles Dan Bilzerian] Ha, you are kidding, where is the challenge?

Make him race Davina McCall.