Founder Breakthroughs

Over the years, as I’ve met hundreds of founders and talked about their challenges, I’ve often had this illusion that there are a million different problems holding startups back.

But recently – as I really dug into it – I’ve realized that there is really 1 problem that  defines whether or not a startup is going to go to the moon – or fizzle out and die.

Today’s guest, Alex Kottoor has made a similar observation. 

The distinction is a...

We’ve talked quite a bit on the pod about Product Market Fit – and hammered home how critical that milestone is to the success or failure of any startup.

But there’s an even more important factor that needs to be considered – and that’s founder market fit.

Before starting his current venture, today’s guest, Shawn Miller,  developed a deep understanding of the problem he wanted to solve through his own direct experiences. 

Not only doe...

Today’s episode features a conversation with Lee Lorenzen, a seasoned entrepreneur - and self proclaimed Forrest Gump of founders - who’s been building startups for over five decades. 

From mowing lawns as a kid to working at Xerox during its golden years of innovation, Lee has seen the tech industry evolve in some fascinating ways.

 In this conversation, we dive into:

 •  How seeing the future at Xerox helped shape his entr...

The gig economy is booming, but there's still a gap when it comes to odd jobs and local services. 

Derreck Stratton, the founder of HUDU – who we first interviewed back in episode #2 – is looking to bridge that gap with an innovative platform. 

During our conversation, we talked about:

·       How Hudu is revolutionizing the way people find help for odd jobs and tasks

·       The challenges of building and scaling a two-sided mark...

The entrepreneurial journey is full of ups and downs, pivots and persistence. Our guest today has lived that roller coaster and is now helping other founders navigate it.

Jessica Lynch is a tech founder turned investor, and during our conversation, we talked about:

- How early entrepreneurial experiences, even failures, can plant the seeds for future success

- The importance of customer discovery and market research before building a ...

Like all of us, today’s guest had to face the hardships brought on by the global pandemic in 2020 – one of which was having her children learn at home instead of in school.

But for her and her kids, something peculiar happened – and they actually thrived in the online experience.

She later learned that other parents and their kids did not, unfortunately, thrive to the same degree – and this led her to try to figur...

The startup journey is full of twists and turns – but it can also present new opportunities as you go down the path.

Today’s guest, Katelyn Alberts started her journey with the idea of building a marketplace – and quickly transformed it into something even greater than that.

During our talk, we covered some really timely topics for any founder:

- How Katelyn, as a nontechnical founder, was able to navigate the toug...

Starting and building companies is an amazing rollercoaster of ups and downs – and for many founders, achieving a successful exit at the end of the process is the ultimate goal.

I’ve been fortunate enough to experience 2 major exits in my founder career – and I learned a ton from both of them. Today’s guest, Mac Lackey – has gone through a total of 6 major exits in his startup career.

Starting out in the midst of the first web explos...

We’ve all seen products over the years that fizzle out or go sideways – and other products in the same category that achieve explosive growth and quickly scale to millions

Likewise, we’ve seen companies enter red oceans with tons of competitors – only to quickly go viral there and dominate. Google did this in the crowded search space of 1998. Facebook did this to Myspace.

But – how do they pull this off?

I’m so excited to bring you to...

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 ...

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...

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...

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 in...

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 runwa...

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 MedicalRecords.com gives us a masterclass on how to stay true to a timeless vision while also leveraging timing to take advantage of opportunities ...

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 ventur...

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 P...

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...

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 sc...