#607 From Homeless Teen to AI Leader: Isaac Cohen's Bold Rise

What if your biggest setback became your greatest setup for success?

In this powerful episode of Talking with the Experts, host Rose Davidson sits down with Isaac Cohen, a man whose story redefines resilience and innovation. From being homeless at 16 to leading a global AI-powered company serving Fortune 50 giants, Isaac’s journey is nothing short of extraordinary.

As the founder of ManyMangoes, Isaac has pioneered breakthroughs in AI for sales, marketing, and recruitment. But his impact doesn’t stop at technology. Isaac transformed his business into a social enterprise—planting trees, creating access to clean water, and building tech for education. It’s proof that scaling a company and scaling good can go hand in hand.

In this episode, you'll discover:

• The 5 turning points that helped Isaac build a multimillion-dollar empire.
• How AI isn’t just for big tech—it’s a scalable tool for small businesses.
• Why purpose and profit are the future of entrepreneurship.

Isaac breaks down complex tech into practical strategies anyone can use—whether you're a startup, coach, or seasoned entrepreneur. He also shares his Engagement Mapping System—a framework that uses AI to pinpoint customer behavior and amplify conversions.

Whether you're navigating startup stress or scaling your company, this episode will give you hope, strategy, and a roadmap for impact.

🎯 Take Action Now:
Connect with Isaac at ManyMangoes.com and follow Talking with the Experts for more game-changing conversations.

 ✨ CONNECT WITH ISAAC

LinkedIn: https://www.linkedin.com/in/isaactcohen/

Website: https://manymangoes.com/

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Transcript

Voiceover | 00:01
Welcome to Talking With The Experts. Here we discuss all things business. By business owners. For business owners. Here is your host, Rose Davidson. 

 Rose | 00:11
Hello and welcome to Talking With The Experts. I'm your host, Rose Davidson from rosedavidson.com.au. It's my very great pleasure to introduce you to Isaac Cohen, who is going to be talking to us about scaling businesses with AI and social impact. And Isaac is... A visionary entrepreneur, he's an AI strategist, and founder of Many Mangoes, a company revolutionizing sales, marketing, and talent acquisition through AI-driven solutions. At 16, he was homeless. By 24, he became SAP's youngest ever executive, closing over $100 million in contract value. In 2018, he launched Many Mangoes, scaling it from zero to serving Fortune 50 of clients while doubling revenue year over year. During the pandemic, Isaac transformed many mangoes into a social enterprise, spearheading initiatives that planted millions of trees, provided clean drinking water and built education-focused technology. Now leading a 300-person team, he continues to push the boundaries of AI, business innovation and global impact. Podcast host inviting for his unique mix of real world experience, high growth strategies and actionable insights that I can't wait to speak with him. Welcome Isaac to Talking With The Experts. 

 Isaac | 01:39
Thank you for having me, Rose. Pleasure to be here. 

 Rose | 01:42
Great introduction. 

 Isaac | 01:44
That's yeah that i couldn't have said it better myself that's i didn't write it so there you go Ha ha! Okay. 

 Rose | 01:56
So you were homeless at a very young age. And so how did you become a global innovator between then and now? 

 Isaac | 02:06
Well, I mean, so when I was 16, it was the 2008 GFC. And so we lost the family home at that time. And my dad lived in Japan and mom lived elsewhere. And so, you know, I must have done everything. 50 different types of jobs, you know, roofing and bricklaying and fishmonger and all kinds of welding, all kinds of different jobs. Different things until I found my thing. It took a while to figure that out. And I think I was blessed to have had to try many things in order to get there. A lot of people kind of settle in for what they have and they kind of just don't leave there. Their thing for their life. 
 So I think I was lucky to have found something that I actually enjoy and am pretty good at. 

 Rose | 02:51
Yeah, being a good old Aussie boy, I suppose, you know, those sorts of, things about you know, marketing, talent acquisition, all those sorts of things. Sort of newer in an Aussie market rather than there are in overseas markets. What ways did you know, at make that happen on a larger scale. 

 Isaac | 03:16
Well, I think sales is sales wherever you are, right? Like it's, it doesn't really matter what you're selling, who you sell, how you're doing it. I started out in door to door sales, where you very quickly get very thick skin. And it's a very different type of no when it's, you know, a door slammed in your face, you know, commission only for like a year. And so I think there I learned to have you know, wide variety conversations with people and then comfortable in whatever situation, doesn't really matter when and who I'm speaking with happy to kind of do that. And so it wasn't until I was 21, when I was picked up by SAP to do like, basic lead gen cold calling basic kind of stuff. But I just hunted. Most of the people I think were a bit more comfortable than I was. I was used to just going after it. 
 I mean, my first quarter there was like 1,200% of targets. And then for the year, it was like 700% or something just because I was constantly hunting, right? That it's, once you get that habit, for door to door, your, You have a different work ethic, I think. 

 Rose | 04:29
Yeah, I think I can probably imagine that. I used to go with my mum sometimes. When she was selling Avon back in the day. And, yeah, it's quite often she'd get, you know, a door slammed in her face or, No, thank you. And yeah, she, You do have to have a very thick skin, I think. But, you know, Australia was a little bit behind the rest of, you know, the US, I'm probably saying more than Australia. I think not. 
 You know, sometimes because of our location, you know, we're away from the main, we were away from the mainstream, but, You know, so things were a little bit different back in, the 50s and 60s and 70s, I would imagine, to what they are now, obviously, because we've grown up a lot. But I want to ask you how AI and engagement mapping are transforming sales and marketing. And recruitment. 

 Isaac | 05:27
Yeah. I mean, it's a, if you, anybody is on LinkedIn, you know, that it's absolutely flooding the market. I think, I mean, even today to previous point, I do think that Australia in terms of advanced sales and marketing and recruitment strategies is still quite behind where America is 70% of our businesses in the U S 20% around Europe and 10% scattered around, including Australia. And that's mainly because it's, just a slower... Slower to adopt, right? Generative AI, I firmly believe it's the single most powerful piece of tech to hit the business world that there's ever been. 
 Like it's... It impacts every single best practice that we've all become familiar with. It impacts every single tool. I think that everything will be redesigned from the ground up. And so one of the things that we... When COVID hit and I went to when I turned many mangos into a social enterprise moved to Africa and did all that stuff we had to redesign the company from basically scratch nobody was outsourcing marketing to an agency so we lost most of our customers and so we fortunately have this great team at many mangos where we can just pivot quickly and jump ship which is which means we look at every problem with a brand new lens right when we look at recruitment we don't look at it as these dinosaurs have been doing the same process for decades. We can look at it as let's redesign the entire thing from the ground up. Generative AI means that we can have hyper-personalized conversations at scale to resonate with people based on their interests, rather than some pitch slappy, copy paste template job. And so I do think that the people who are not Trying to change every best practice they have with generative AI. I don't see a future there. 
 Like I don't see how they can possibly make it. 

 Rose | 07:23
But from, you know... I've only started using AI for maybe the last 18 months or so. I'm sure that AI was around before then, but we probably didn't realise it. I've been using chat GPT a lot and I really love it. And, you know, they're always upgrading it. Constantly and you know new features all the time and you know i even gave mine a name the other day and it loved my name that i gave it Cut. 

 Isaac | 07:54
What did you give it? What was the name? Dot. 

 Rose | 07:58
Dot. Ouch. Scott. Yay. And it's... I did ask it, did it have a name? It said, no, I'm just chat GBT. I said, well, I'm going to call you Scott. And it said, that's a nice name. I like that. 

 Isaac | 08:11
That's great. And then you can have long dialogues, have a little chit-chat after dinner. 

 Rose | 08:16
Absolutely. But, you know, in just the short time I've been using it, there's so much advancements in technology. Using it. And I had a guest on a couple of weeks ago who uses in movie production. And uses it in television programs and stuff. And I thought, my God, why would you use AI? 
 And then I... Did a bit of research and you know they can you know do videos and all sorts of things and I’m thinking well in marketing how can you use ai in marketing and recruitment So maybe you can explain that to me. 

 Isaac | 08:53
Well, I think marketing, sales and marketing is probably where it's most used today. But speaking with someone from Microsoft a few months ago, and they were telling me about the acquisition of it. And when they were coming up with GPT, they were using it in the gaming industry or something. And so you were in a game and you'd say, Hey, make me a sword or whatever. And so it would come up, create different items for the game. And so I do think it It's very relevant for all lines of business, but in particular, sales and marketing and recruitment is important. Is the most relevant because it's conversational, right? When you're in sales, when you're marketing, when you're in recruitment, which is just sales really, it's conversational. You need to build relationships. You need to find a reason to engage with someone. And often that's one of the hardest parts of sales is coming up with a good reason to speak to someone more than, "Hey, I want to sell you something." And so with generative AI, you can start to analyze large amounts of data about a and prompted to say, find me something that they're interested in. Find me some icebreakers. Find me a reason to engage. And 99 times out of 100, it'll come up with better ideas than you did. That's where it's really helpful. But if you combine that process or that activity with automation, all of a sudden you can analyze every CEO in all of Australia and find a good reason to engage all of them. Build your secret sequences around that instead of sending out a, you know, template message, 10,000 CEOs could now have a personalized, hey, Rose, I saw your last thing about this and how you moved house. 
 So it's most particularly relevant for sales marketing recruitment because sales marketing recruitment is conversational. Which is what language model is. It's about interacting and finding the next thing to say. 

 Rose | 10:48
Yeah, I get that. It's an interesting concept about how we're going to use it moving forward, I think. 

 Isaac | 10:58
Yeah, I think what's been really exciting, the exciting developments on our side. Has been this combination of agents. 
 So when you configure an agent, it does a series of tasks almost autonomously. It'll continue with the work until it completes a certain job. 
 So you can design these agents to be a very junior version of an actual employee. But when you combine multiple agents and let them talk to each other, you can have more functionality and capability than an entire department. 
 So I think before the end of this year, I think we're going to see most companies finding creative ways to adopt a swarm of agents within departments or entirely new departments that don't exist today because there are so many agents, right? So configuring new strategies, configuring new content deployments, figuring out, you know, what to do with sales and logistics. And that's one of the things that I'm doing next week in Japan, which is taking a business, seemingly technologically advanced culture, the Japanese, yet they are the biggest fax users on the planet. 
 Like they have all of their operations, logistics and purchases and input. Everything is done through faxes, right? Not even digitized faxes. They're literally the, There's no, not even e-fax. It just comes out of, I've never actually sent a fax before. And so when I went over there a few months ago, it was like, This is... This is the same process as 50 years ago, right? 
 And then we're like, yeah, this is exactly it. So being able to digitize that content and use generative AI to segment all of the information to then automatically distribute it throughout an organization, you're talking about not a few percentage points of efficiency. You're talking about a multiplier effect of efficiency and productivity throughout a company. 
 So I think the impact is significant and it's going to be really interesting to see which regions and cultures Adopter the fastest. But those that do will we'll. 

 Rose | 13:12
Win absolutely Isaac what are some key lessons From scaling your many mangoes from zero to multimillion dollars, what lessons did you learn along the way that can help our audience? 

 Isaac | 13:26
.. I mean... The two big ones would be fail as fast as possible. 
 Like build your prototype, build your stuff and get it out there. And as much feedback as you can get from actual people, the faster you'll iterate, right? Whatever product you decide to deploy, most likely it'll be a hunk of junk compared to what you're going to end up having. 
 So the faster you can get that feedback and iterate will make you competitive. And that breeds a culture of innovation and staying on top of it and trying to be a creative problem solver. That's a big one, which is fail fast. And the other one is finding, I call them my diamonds, but finding the diamond team members, the people who are have had... A lot of experience, potentially challenging experiences, but able to Be dependable, right? A really reliable team means the difference between trying to do everything yourself and actually trusting people to have a high quality results with similar values as you do. 

 Rose | 14:32
Yeah, it's one of those challenges too is to find the team members that you can trust and find those people that can do stuff that you can't do and do it better than you can. Could probably do yourself. And a lot of CEOs don't, want to let go of those little tasks and they, you know, micromanage. And I think they're being silly to themselves. They're being silly to their companies. 

 Isaac | 14:57
Hey, you, your roof is so narrow. It's so short. If you have that mentality that the founder syndrome was a core, right? Trying to do everything and being it, you know, you'll never ever be able to scale if you try to do everything. It's that simple. But even with hiring and finding great people, I think that first piece is key as well. Fail fast. 
 Like I'm, I said to my team when we put a little powwow thing we're doing here now, and it's like, you're going to have, Most interviews are just a waste of time. They're so prepared. They sound so amazing in that interview. 
 So give them a test. Give them a trial. Give them something. Prove their worth. Fail fast. Hire someone really quickly, but get rid of them if they're not the right person. Being able to move that quickly means rather than risking it for nine months with the potential, you know for sure you've actually tested out the right people. Fail fast. 

 Rose | 15:53
Absolutely. I used to work for a government law enforcement agency some years ago. And they, in one of the recruitment press interviews, groups, they hired all these university graduates. And, you know, they did really well in the training because, you know, they were very smart. They couldn't do just the basic everyday mundane tasks. Task it. And, you know, there was always people picking up on their mistakes. And, you know, just because they, prove themselves in an interview and through the training doesn't mean that they're suited to the position because these people just were not. And I think that. 

 Isaac | 16:34
Could have easily been avoided if they give a proper interview test and actually say, hey, do the job for two days, three days, whatever, you'll be paid. They would have identified that months earlier. 

 Rose | 16:46
Absolutely. Yeah, I couldn't agree absolutely more. 
 So you have this social enterprise. So Many Mangos is a social enterprise. And so how can businesses drive profit and global impact simultaneously? 

 Isaac | 17:02
I'm a big believer that it is good business to do good in business. I think that there's no reason not to. And like, I've been doing charity stuff since I've been working forever. But today, we, in fact, right now, we just finished, we've got 9,800 and whatever followers on LinkedIn. And so by the time this thing airs, it'll be over 10,000. 
 So you'll be able to see some of this content. But we're donating, we've gone out and collected one kilogram of ocean plastic for every one follower. 
 So 10 tons of that's a lot of bloody ocean plastic. And then we go out and we recycle it and we clean it, upcycle it, we turn it into other products, and it creates little businesses for the communities out here. And so instead of doing you know, hey, great, we did 10,000 vols. 
 Well, why not make it something that's actually good for the people and the planet, which in turn is going to be great for business. It's a thing that shows who we are, right? It's about your values. And I don't think it needs to be perhaps as dramatic as 10 tons of, right? It can be as simple as 10 trees, go out and plant some trees, go to a food day, right? It costs you nothing. And it's like, it would impact the lives of lots of people. It's so... There's a nonprofit I run with my brother, We Make Impact. One of the things we talk about with people is the hardest part is that first step. And making a positive impact. Once you do, it's addictive. You'll see yourself constantly doing more and more. 

 Rose | 18:42
Yeah, I know that feeling. I co-founded a social enterprise, Healing Through Love, and we provide free paper day events for domestic and family violence survivors. We do that on an annual basis. And we get vendors to come in from Australia healing modalities and, you know, we get government organisations in to offer their services free for the day. And, you know, the impact that it's had on these survivors, it's absolutely amazing. And, you know, it makes me feel just so grateful. Warm and cuddly inside because you know I’ve helped somebody you know overcome something you know something traumatic so it's we feel great about it and so I know what the feeling is when you do something good for someone how good it makes you feel. 

 Isaac | 19:32
Now you've done it. You'll do it forever. You'll do it for the rest of your life. Absolutely. It's, there's no way that thing is going to leave you because you've taken that first step.

 
 Rose | 19:43
Absolutely. No, I agree 100%. If you want to find Isaac, you can find him at manymangos.com. And that's his website. And he's on LinkedIn at Isaac Cohen. And Go and reach out to him. I'm sure he'll have lots to say to you if you reach out and have a discussion about either a social enterprise or how AI can help you in your business. Isaac, do you have anything else you'd like to share with us today? 

 Isaac | 20:11
No, look, I'm grateful for your time. Great questions. I do hope if anybody is... Anybody who's watching this and wants to try to make more positive impact, I'd be more than happy to come up with like brainstorm creative ways for you to do it. It is easier than you think. And it does make a big difference to your business, to your mental health, physical health, and it helps people. I'd love to have more of those discussions. 

 Rose | 20:37
I think it's been a pleasure. Thank you so much for joining me today. 

 Isaac | 20:41
Thanks for having me, Rose. 

 Rose | 20:42
Bye. 

 Speaker 4 | 20:44
You've been listening to Talking With The Experts, hosted by Rose Davidson. Make sure you have a look at our back catalogue over at talkingwiththeexperts.com. And be sure to subscribe to our podcast so you don't miss out on any episode. We look forward to your company next time.