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 around whether or not you achieve product market fit or PMF.

And the path to get there – Go To Market or GTM – requires an amazing amount of vision, action, and most importantly persistence.

Alex and I had a fascinating discussion where we boiled down what separates founders who are able to make it through this journey – and those who give up.

How to know when you need to buckle down and push harder – vs when you need to step back and get new options.

And why startups need to keep their energy focused on GTM and not get sidetracked by all of the other temptations along the way.

It was a fascinating discussion – and I hope you get some gems out of it.

Links:

Alex: https://www.linkedin.com/in/alexkottoor/
Dena Startup Lab: https://www.denastartuplab.com/

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 does founder market fit make it easier to persevere when the going gets tough – it also makes sure you have the right lens to catch opportunities as they arise, and to separate the signal from the noise.

I had a ton of fun talking about Shawn’s background – how it informed his idea for inbound – and how it has drastically increased the odds of the company achieving product market fit.

I gained so many great insights talking with Shawn – and I hope you do as well.

Links:

Shawn Miller: https://www.linkedin.com/in/shawndavidmiller/
Inboundr: https://www.inboundr.ai/

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 entrepreneurial journey

• Navigating major technology trends over the years

• The tension between seeing the future and living in the present

• Building startups with a mission-driven mindset

• How founders can take advantage of a non-traditional funding approach outside of VC circles

It’s an engaging discussion filled with valuable insights and stories from Lee’s incredible career.

Links:

Altura Ventures: https://www.altura.net

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 marketplace

· The importance of focusing on your core markets before rapid expansion

· How AI is being integrated to make the user experience seamless

· The potential for Hudu to enable a new kind of "physical nomad" lifestyle

· And the journey from launch to achieving product-market fit

You can learn more about Derreck and HUDU at:

HeyHUDU.com

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 product

- How to pivot a business model when faced with major external challenges

- Navigating the emotional and practical challenges of the M&A process

- How founders can set themselves up for success by learning from those who've gone before them

Jess shares some incredibly valuable insights from her own founder journey and her current work investing in and accelerating promising startups.

Links:

Jessica Lynch: https://www.linkedin.com/in/jessicallynch/
Raiz Capital: https://raiz.vc/

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 figure out what worked for her – and how she could share that. This inspired the creation of Edify – a tutor matchmaking service which is on a mission to help neurodivergent kids everywhere thrive in an optimal learning experience.

We had a fascinating conversation where we talked about how she was able to bottle the inspiration – and figure out what actually made the experience work. How putting extra effort into matchmaking up front pays dividends later on, and how she is working to scale the business without losing the magic at its core.

I learned a lot from the interview – and hope you do as well.

Links:

Priya: https://www.linkedin.com/in/priya-tron/
Edify: https://www.edifylearningspaces.com/

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 tough question of whether to hire a tech team or recruit a tech founder – and how she discovered an even better approach.

- How to go from seeing a problem that needs to be solved – to deciding to take action on it yourself.

- What to do when you get started – and how to define your MVP

- The challenges of building a 2 sided marketplace – and knowing how to recruit participants on both sides.

- How adding a community mastermind to the mix can add huge value to the core members of the audience – and generate more revenue to help grow the business

- The importance of getting the formula right in one location – to achieve “density” – before scaling

Links for Katelyn:

VERVERY: https://www.ververy.com/
LinkedIn: https://www.linkedin.com/in/katelynalberts/

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 explosion of the mid-90’s, Mac quickly built and sold his first company – and has then learned how to capitalize on opportunity after opportunity since.

I had a fascinating conversation with Mac about the ups and down, the huge takeaways – how he improved his craft with each exit. And – how we all can learn from his experiences to drive something he called optionality into our own startup experience.

I hope you get as many gems out of our conversation as I did!

Links:

Exit DNA: https://exitdna.com/
Book: https://exitdna.com/book/