Founder Breakthroughs

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...

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 lis...

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, t...

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...

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 t...

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...

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 i...

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 spac...

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 actual...

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 us...

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 o...