Podcasts Where Hosts Share Stories of Big Wins & Losses
Whether your thing is investment, entrepreneurship, or gambling, hearing real-life success stories from others can help provide inspiration and even some guidance. Fortunately, there are plenty of podcasts out there that promise exactly this. They are either hosted by successful individuals or regularly feature them and give invaluable insight.
Podcasts are a convenient way to stay on top of the latest news and enjoy interviews with relevant guests and industry insiders. Podcasts are covering every type of money-winning or money-making activity, from real estate investment to slot gambling.
Winning Big
Online casinos continue to increase in popularity, due to their opportunity to generate life-changing money for players. Progressive jackpots can total millions of pounds, and most games are easy to learn.
Furthermore, GamesHub’s list of UK casinos not on Gamstop includes sites that do not have the usual verification requirements, which means greater privacy as well as expedited signup processes.
The sites include poker, which is a popular podcast topic, especially around the WSOP series, along with slots and other online casino sites. Online gaming expert Maelis Hartley points out, however, that online slots remain the most popular games at casinos due to the massive jackpots and easy rules.
We Study Billionaires
There are a lot of ways billionaires make their money, sometimes even by accident. The We Study Billionaires podcast series looks at some of the world’s richest individuals and families to determine how they made their money, providing insight and analysis.
Listeners can also enjoy regular interviews with some of the podcast subjects, giving an even more personal look into their routes to financial wealth.
The show is hosted by Stig Brodersen, Preston Pysh, William Green, Clay Finck, and Kyle Grieve, and one regular feature that listeners will enjoy is the Richer Wiser Happier series. Best-selling author Green interviews some of the most successful investors of all time.
Mad Money
Mad Money w/ Jim Cramer is the podcast version of the CNBC show. Hosted by Jim Cramer, the show has plenty of features, particularly pertaining to stocks and investments.
The show gets generally good reviews from listeners, although some criticise it for having too many CEO interviews – but, if you’re looking to replicate their success, these interviews can be a goldmine of information.
PokerGO Podcast
If you’re more into cards than balance sheets and prefer hearts to tickers, the PokerGO podcast will be better suited to your tastes. Donnie Peters and Tim Duckworth host the show, which airs daily during big WSOP events.
PokerGO covers news from all the major tournaments, and this includes interviews with some of the latest and biggest winners on the tour.
They might not give away in-depth playing tips – they are trade secrets, after all – but listeners can hear about how it feels to win and maybe pick up a few pointers on how to improve their game and their poker standing.
PokerNews Podcast
The PokerNews podcast is another regular audio production that delves into the world of poker. It offers tips and strategies, as well as specific guides on how to play, but it also looks into the lives and careers of some of the most famous poker players.
The PokerNews podcast will be popular with listeners who want a broad understanding of the circuit.
Lottery, Dreams And Fortune With Timothy Schultz
We talk about lottery winnings and other major winnings as being life-changing. Even the most grounded individuals will inevitably make some changes to their lives and lifestyles, and Lottery, Dreams and Fortune with Timothy Schultz looks at big prize winners to see how they won their money and the impact doing so has had on them.
Schultz himself won $21m on the US Powerball, which means he has first-hand knowledge to impart to his readers.
Won In A Million
Here in the UK, the National Lottery has the power to change lives and, since its inception in 1994, it has created more than 7,200 millionaires around the country. The National Lottery itself has its own podcast, Won In A Million.
Hosted by comedian Ellie Taylor, the aim of the relatively new show is to show the positive effects of the Lottery, which includes some tales of winning players.
Gambling With An Edge
Gambling With An Edge is a gambling podcast hosted by professional gamblers Bob Dancer and Richard Munchkin. Recent guests have included a video poker player who was able to exploit a specific video poker game to turn a profit, as well as a professional pool player and an advantage play analytical expert.
Listeners can enjoy tips on tightening their own gambling strategy while hearing insightful stories from others who have done so.
By podcast24.co.uk - Published 9/19/2025
Updated 9/19/2025