
Episode #153
The AI Hustle with Jason Wright
In this episode of Keep Hustling, host Aaron Gordon sits down with Jason Wright, founder of Intentionally Inspirational and an early adopter who was testing AI inside ActiveCampaign five or six years ago, well before most people had heard of ChatGPT. The feature was predictive sending, it beat regular sends by four to seven percent, and nobody cared at the time. What makes the conversation useful is that Jason has since talked himself down. Back in March he was telling everyone to get on the bandwagon or get left behind, working harder than he ever had in his life. Then he noticed that nothing goes straight up forever. His position now is narrower and more honest: AI is excellent where the answer is black and white, and useless where it is not. Ask it how many ounces are in a pound, not how to fix your marriage. From there they get into his book on crushing fear and self-doubt, the choose-your-hard argument for betting on yourself, and a long detour into cigars and bourbon that turns out to be about the same thing. He closes with four words: go or get off the pot. Get To Know Jason Wright Jason Wright is the founder and CEO of Intentionally Inspirational , the marketing and automation agency he launched in 2015. He did not start out as an AI guy. He started out as an entrepreneur who was tired of watching good businesses fail because of bad marketing. It was not his first business. His first taste of entrepreneurship came at fourteen, running lawn care and landscaping, with more fishing tackle as the motivation. He was told to go to college, get a degree, and get a real job, so he did. After seven years in corporate America, he had enough for one lifetime. He built Intentionally Inspirational on one belief: that small businesses and entrepreneurs deserve the same quality of marketing that big companies pay millions for. The difference, as he puts it, is that they actually do the work themselves. No white labeling, no outsourcing to an overseas team, no faking it until they make it. Over the past ten years the agency has worked with more than 725 accounts across ActiveCampaign, GoHighLevel, MailChimp, ConvertKit and others, building hundreds of funnels, running Meta ad campaigns, and setting up email automation systems for service businesses. Then AI showed up and changed everything. A few years back they were dabbling with machine learning features inside ActiveCampaign, well before the current wave. When it became clear this was not just hype, they went all in. Today the work comes down to two things: fixing the offer and filling the calendar with qualified leads, with AI and automation as the method rather than the point. He is the author of The Backwards Route To Forward Progress: 7 Solutions For Crushing Fear, Self-Doubt and Limiting Beliefs. He also hosts the Intentional AI Daily podcast, where he shares practical AI strategies, real world workflows, and honest takes on where the technology is headed. He runs the Smoke, Flow & Grow community on Skool, where cigars, smoked meat, bourbon and a little bit of business get discussed around the fire pit. With his wife he recently launched Bluebird Keepsakes, making personalized keepsakes on three lasers. He lives in St. Marys, Georgia. Website - https://intentionallyinspirational.com/ LinkedIn - https://www.linkedin.com/in/thejasonwright/ Youtube Facebook Instagram Buy Jason's Book Jason's Podcast Smoke, Flow & Grow on Skool 3 Key Listener Takeaways 1. Put AI in its lane. Jason's test is whether the answer is black and white. Numbers, analysis, a screenshot of a program you have never opened, how many ounces are in a pound while you are cooking. All of that it handles instantly. Ask it about your marriage and you are, in his words, asking a pizza for advice. It can also argue with you convincingly while being wrong, so run everything past your own logic test. 2. Choose your hard. His answer to anyone stalling on a leap. You can live a hard life from trying something and having it fail, or a hard life working for somebody you hate inside a safe and miserable job. Either way it is hard, so pick the version you would rather be living. He has failed more times than he can count, and his wife stopped counting the business ideas a decade ago. 3. Culture is not a waste of time . The cigar lounge is what Jason calls the great equalizer, where a blue-collar guy and somebody extraordinarily wealthy sit next to each other and nobody cares who anybody is. Aaron adds the part that makes it rare: forty-five minutes where nobody reaches for a phone. Find your version, whether that is a fire pit, a fishing boat, or a golf course, because the ideas tend to show up there. Show Overview 00:00 Meet Jason Wright 04:29 Cigars, bourbon, and business around the fire pit 08:19 Where AI helps, and the lasers at Bluebird Keepsakes 10:45 Getting AI to explain fourth grade math 15:34 Choose your hard 17:41 The cigar lounge as the great equalizer 22:11 What to smoke if you are just starting 26:07 Why culture changes your business life 28:01 Wrapping up with listener engagement






