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Founder Breakthroughs

Author: Jeff Durso

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Every week, Inc 500 Serial Entrepreneur Jeff Durso interviews brave founders, uncovers their epic stories, and elicits profound insights about what has helped them achieve breakthroughs in their business.

34 Episodes
If you’re involved in selling – and especially B2B selling for a SaaS business, then you’re going to love today’s episode. In the last episode, we talked with Stephen Steers about how storytelling is important to sales. Today’s guest – Matt Wolach – shares a masterclass on another aspect of B2B sales that will help you massively increase your close rate.In sales, it can be tempting to share all of the unique features and bells and whistles of your product. Especially after you’ve spent to much care bringing it to life. But Matt explains how a different frame – based on deep curiosity for your customer’s challenges – is going to help you improve your results.I had a blast talking to Matt – and learned a ton of nuance along the way. I hope you get some gems as well.Links:LinkedIn: 
There’s one skill that every founder has to master in order to build a successful startup.I’m talking – of course – about sales. But – there are a lot of misconceptions out there about what sales is and what it isn’t.Today’s guest – Stephen Steers – has mastered the art of Startup Sales and codified it into a method he calls Contact Sales.During our discussion, we talked about the importance of story – and why it’s critical to help your prospect see themselves in the story.We talked about how to eliminate the pressure of closing – and help your prospect from the same side of the table.We talked about how to structure your sales call for maximum effectiveness – and a lot more.It was a value packed discussion – and I hope you enjoy it as much as I did.To learn more about Superpower Storytelling & Stephen:
The modern startup ecosystem has been evolving for decades – since the evolution of Silicon Valley from farmland to the hardware companies of the 60’s and 70’s – to the modern tech startup space of today.But – even after all of these years, a founder looking for support can still feel like they’re living in the wild west. At the elite levels, accelerators like Y-Combinator and Techstars certainly offer transformational support. But outside of the top 1% or so – the rest of the space can be a bit confusing.Today’s guest, Jonny Boyarsky is looking to help founders cut through the noise and get better advice.His company, called “Literally Helping Startups” – is, wait for it – literally helping startups make sense of the journey.We had a great in depth conversation around all of the challenges founders face today, what they can do to make more sense of the world – and what Literally Helping Startups is doing to help move things forward.
We’ve talked a lot on the podcast about the importance of asymmetric upside – or luck – in helping to drive entrepreneurial success.Today’s guest, Vlad Mkrtumyan, has made stacking the deck into a science in his ventures.In his first company, he launched an app featuring Drake quotes that got 2,000 downloads in week 1 - then he rinsed and repeated the process into hundreds of thousands of downloads.He then turned what he learned into a method he uses for evaluating and executing new opportunities to make sure he and his agency’s clients are constantly in the flow of asymmetric upside.We had an amazing discussion going deep into a whole bunch of rabbitholes – peeling back the layers of the onion and finding new insights on what makes founders win – and getting dangerously close to solving puzzles around success in general.I had a blast talking to Vlad – and I hope you enjoy our discussion as well.
Every startup needs to make money – but some startups are architected with a much bigger purpose in mind.Today’s guests, Mike Mills and Nick Spoors of Infinitary Fund – have found a unique way to fund their mission.Their core innovation has enabled them to sell a product today that gives them cashflow and runway to build the business – while also funding a Think Tank that is going after some pretty amazing breakthroughs.Their runway business keeps the lights on – and their think tank enables them to shoot for the moon.I can’t even imagine how much innovation could be unlocked if more companies were designed this way.We had a fascinating discussion going deep on this new model for doing business – and I hope you find it as inspiring as I did. 
Timing is one of the hardest challenges for founders. Execute an idea too soon – and you’ll run out of runway before someone gets there when the time is right.Execute it too late – and you face still competition from the incumbent that got there first.Today’s guest, Ace Bhattacharjya of gives us a masterclass on how to stay true to a timeless vision while also leveraging timing to take advantage of opportunities as they arise.Over 20 years, he’s built multiple successful iterations of the business – while also being poised to pounce on huge trends as they’ve emerged.Ace & I always have fascinating conversations – and I’m super excited to be sharing this one with you. I hope you gain as many takeaways from our conversation as I did.
One of the common themes I see with top entrepreneurs is that they find a way to get experience from multiple viewpoints within the startup ecosystem.Today’s guest, Stephane Nasser of Open VC is no exception – having had stints from the large corporate world building software for startups, then working within accelerators to help startups get launched, then – of course – working as an entrepreneur, and finally landing in the venture capital side of the world.During our talk, we did a lot of deep dives around all of these angles while also pulling out the common themes that apply across all of them.I gained a lot of great insights from his wide range of experiences across the startup world – and I hope you are able to get some gems out of our conversation as well.You can learn more about Stephane and Open VC here:OpenVC: https://openvc.appStephane:
Today’s guest, Peter Mann, found out that he had autism in a late diagnosis as an adult. But – buried in this so called diagnosis was actually the operator’s manual for his supersuit.While working a full time 8-5 at Dell, Peter was able work another 8 hours per day launching his first side hustle – and he was able to find flow and focus throughout these long days.What might be exhausting or cause burnout for others – actually lit Peter up with motivation and purpose.Over several decades, he has turned this drive into multiple successful businesses – including his current venture, Oransi, which he decided to start when his son had trouble breathing and he wanted to find a better way to solve the air purification problem.We had a fascinating conversation about how Peter has been able to apply his hyper-focus to methodically build and grow several successful businesses. 
There are a lot of paths into the world of entrepreneurship, but today’s guest has one of the most fascinating ones I’ve found yet. While running a popular Miami nightclub, Shaun Gold had front row seats to a parade of some very interesting and diverse people. By being curious – and making connections – Shaun built a network that would take him on a whirlwind through the entrepreneur world. From startup founder, to investor, to the world of Hollywood and screenplays, and even a stint on jeopardy – Shaun’s ability to connect with varied people have taken him on some pretty amazing adventures.During our talk, we discussed the common thread that ties all of these experiences together – and also how they apply to the current environment for funding and launching startups.
I’ve gotten to talk with a lot of amazing founders on the show over the past 6 months.In today’s episode, I had the chance to speak to an expert with a unique vantage-point and mix of experiences.Elad Granot is a serial entrepreneur, the Dean of the Boler College of Business at John Carroll University, an active investor in startups, and also host of the Bottom Line podcast.From his unique vantage-point as the dean of a business school – and an investor – Elad is able to keep his pulse on what upcoming entrepreneurs are thinking about – and then apply that knowledge to his ongoing funding thesis.We had a great conversation talking about what things have changed over the past 3 decades, and what principles have stayed the same.And we also how the major disruptions of the day – like Artificial intelligence – are increasing the pace of change in the startup world.It was a super fun talk – and I hope you learn as much from it as I did.
One of the themes that keeps re-appearing on the show is that industries that look like they have been locked down for years or even decades – can suddenly go through a renaissance and lead to a new jump ball.Today’s guest is taking advantage of a massive shift that’s happening in the online selling space.As influencers flock to sell items on the multiple prominent marketplaces, they’re stuck with the challenge of managing listing across 4 or 5 networks for every product they sell.With SellStuff, David Brown is building a platform to tackle this issue head on. We had a fascinating discussion on how he leveraged his experience at big tech firms to conceive of and now launch his new app which will enable influencers to enter their information once – and list across the marketplaces.Beyond removing friction – he sees the opportunity to help transform the marketplaces themselves – and the community of influencers that sell on them.I got so many gold nuggets out of our discussion – and I hope you learn as much as I did.
It’s easy for founders to look at an industry and think that you’ve already missed the boat. I could have done this with travel in 2003 and missed the destination wedding trend – and it would be easy to conclude that ride management has already been won by Uber and Lyft.But today’s guests – Zach Castaneda and Steven White are approaching the transport space with a unique spin that is starting to catch waves. As industries mature, they leave holes for new entrants – and that’s exactly what Zach and Steven see in transport.Their company Shofeur is helping re-invent a segment of the transport space by helping fleet operators level up with their customers.We had a fascinating talk – where Zach and Steven explained what was missing in the space, why they saw the opportunity, and how they are gaining steam going after it with Shofeur.
On July 16, 1945 at 5:29 am – the world changed.Up until that point – there was strong theory supporting the idea that enormous amount of energy could be unleashed by splitting an atom.At 5:29 on that day – that theory became indisputable reality – and the world was never the same.That test on July 16, 1945 was code named Trinity – and today we’re going to talk about how founders can pursue their own Trinity moment in their startup – and how this type of nuclear demonstration can give them huge momentum.
For most startups, the main task of launch and validation is to figure out if the market has any interest in the idea at all – and if it’s possible to gain traction. Today’s guest, Rachel Cossar – took a different approach. She was already operating a successful coaching practice helping her clients optimize nonverbal cues during sales calls.She knew this process was valuable - but her question was – could it be automated through technology and AI? We had a fascinating conversation about how this question led to the formation of Virtual Sapiens – and how she has been able to transfer her existing validation of her process into a way to deliver the same value through AI.She’s had an amazing step by step journey – from initial validation of automating the process – to multiple iterations that have built trust in the AI and started to deliver results to her clients automatically.I learned so much in this conversation – and hope you do as well.To learn more about Rachel and Virtual Sapiens:Virtual Sapiens: Cossar:
Todd Sullivan is co-founder and CEO of ExitWise. After building and exiting a series of his own companies, Todd now helps founders plan and maximize their own exits when the time is right.During our talk, we covered:-       How solving your own burning need can be the best launchpad for a startup-       How decisions you make now can set you up for a strategic acquisition later down the road-       The dangers of depending too much on someone else’s ecosystem – and how to mitigate them-       The importance of timing in acquisition – and how one founder was able to 20x their exit outcome by planning this well-       How to manage the 3 different types of exit scenarios-       Why bringing an experienced M&A team to the table can make a deal go much smoother-       How to make sure time works for you and not against you in any deal process-       And how the current funding environment is affecting M&A – and which companies are poised to winYou can learn more about Todd and Exitwise here:- ExitWise: LinkedIn: Cashing Out Podcast:
One morning just over 11 years ago, I met up with my friend Dr. Michael Connell in a Panera to talk about a startup idea he was working on in the education space.He told me about a groundbreaking research study that had been done during the 90’s that could have revolutionized how children learn math – but how previous attempts to deliver it at scale had failed to move the needle.During our breakfast, we pondered whether the newly introduced iPad could create an opportunity to take a new approach to bringing the research to life.And thus began one of the most incredible journeys of my career.A year later – we released Native Numbers into the iPad app store. 6 months after that – it ranked up to #2 in the education section, and 10 years later – it’s helped over 700,000 kids and counting learn math.On this episode – Mike and I talk about the story behind Native Numbers – and also get some of his prescient insights about what’s happening in the ed tech space.
Akash Magoon's company Adonis is innovating the healthcare billing space – hoping to reduce enough friction so it feels much more like stripe than what patients and providers have to deal with today.We hit a lot of great topics today:-       How having a strong relationship with your co-founder can set the stage for candor in your startup-       How healthcare space has changed in the past 10 years – and how to approach a space once the low hanging fruit has been picked-       How the proliferation of best of breed point solutions can create an integration burden on the end user-       What to do when an ecosystem has misaligned incentives-       How a diagnostic can be the perfect way to open a client relationship and uncover the most pressing challenges-       The importance of knowing whether your market is in a build or buy cycle, and-       Why startups should earn the burn if they’re looking to raise moneyYou can learn more about Adonis at:
Matthew Turner is the author of the book Beyond the Pale. In writing his book, he interviewed over 100 founders to learn how they found balance in their lives as entrepreneurs. We talked about:-       The downside of so called hustle culture – and why founders should try to avoid it-       How founders can tap into the creation vortex – to drive their best ideas-         How sometimes skills we take for granted are actually super valuable to our customers-       The right way to frame mistakes so you can make the most learning from them-       Why it’s important to have a clear definition of what success means to you-       The importance of having something called a “Hell Yeah” – and how to use this to drive all of your important decisions.It was a fun conversation – and it was super insightful to hear what Matthew learned from the 100+ founders he spoke with.
David Sorbara is the founder of Barkley HQ – a software as a service product that helps pet groomers run their businesses.I learned so much from David – not just about his experiences growing Barkley HQ into a successful business – but also in how he is working to take his experience to launch even more businesses now – all while continuing to benefit from BarkleyHQ.During our talk, we discussed:-       Why some businesses still use pen & paper to operate – and how this spells opportunity for startup founders-       How making your customers customers look good creates a halo for your customers – and for you-       How you can get started with youtube, organic, and other cold outreach methods-       Why it’s important to know where your customers are – so you use the right channel to communicate with them-       How leverage comes from actually solving customers problems at a deep level-       And – how to go from 1 successful SaaS business to launch multiple new onesIt was a super exciting discussion – and I learned so much about how to go deep on customer experience to create a great startup.
Mark Herschberg - has worn many hats in his career including Founder, Chief Technology officer, Author, and Instructor at MIT.A lot of episodes have focused on the startup, today we went deep on the path and growth of the founder behind the startup.We talked about:-        How the startup world presents challenges differently than how you were trained in the past-       A great method for modeling a problem so you can then figure out how to solve it-       The open ended nature of startups – and of the career of a founder, and how to navigate through this-       The magic of patterns – and how to get better at spotting them-       How to intentionally build your skills as you navigate the founder career path-       And quite a few surprises in terms of which companies win – and which ones get defeatedMark's Resources:1) The Career Toolkit Book: Brain Bump App:
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