Founder Breakthroughs

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: https://www.virtualsapiens.co/
Rachel Cossar: https://www.linkedin.com/in/rachel-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 win

You can learn more about Todd and Exitwise here:

- ExitWise: https://exitwise.com/
- LinkedIn: https://www.linkedin.com/in/toddfsullivan/
- Cashing Out Podcast: https://podcasts.apple.com/us/podcast/cashing-out-an-exitwise-m-a-podcast/id1642784919

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 money

You can learn more about Adonis at:

https://tryadonis.com

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 ones

It 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 defeated

Mark's Resources:

1) The Career Toolkit Book: 

https://www.thecareertoolkitbook.com/

2) Brain Bump App: 

https://brainbumpapp.com/