David's startup failed. But he had everything going for him: a solid thesis, $16M in funding across 3 rounds, $1.5M in ARR. At a high-level it seemed like everything was going the right way. And yet, it didn't work out.

This is what happens to 95% of startups. On thhis show, we mainly speak with the top 5%-- the ones where things went right and everything worked out. But you tend to learn more from failures than successes.

On this episode, we go deep with David to see what building Tandym was like, why it ultimately didn't work, and what he would do differently the second time around.

Why you should listen:

• Why you should always start with the model that requires the least capital
• Why you need to be a number one priority for your customers
• Why even hitting $1M ARR doesn't mean you will succeed.
• Why you need to pivot quickly as soon as things are clearly not working. i

Keywords
product-market fit, startup journey, fundraising, fintech, brand partnerships, business model, sales challenges, urgency in sales, Tandem, lessons learned, startup, fundraising, product strategy, compliance, revenue growth, entrepreneurship, lessons learned, business pivot, mid-market brands, capital management

Timestamps
(00:00:00) Intro
(00:03:30) The Origin of Tandym
(00:09:26) Taking the Leap
(00:11:37) The Business Model
(00:17:22) Developing the Product
(00:21:05) Struggling to Create Urgency
(00:26:50) Raising Rounds & Shifting
(00:35:11) First Signs of Problems
(00:39:01) The Product that we should've launched
(00:42:12) How it All Ended
(00:49:56) Final Thoughts & Advice

Send me a message to let me know what you think!

Justin sold his first bootstrapped startup for over $10M. He raised $2M out of the gate for his second and then grew from $250K to $3M ARR in one year. He raised $40M in total, including a Series B from Bessemer.

And yet, just a week before recording the episode, he shared a post on LinkedIn about a recent panic attack that left him frozen for 15 minutes. It turns out, the sheer pressure of running a startup gets to him-- like it does to most founders-- and shows up in the forms of panic attacks. Fortunately, he's getting better, but like all of us, mental health is something he has to grapple with, despite all the success he's had.

We discuss mental health in startups, what it takes to be successful, the difference between bootstrapping and the VC-backed route, and how he grew his startup from nothing to 8 figures in just 4 years.

Why you should listen

- Mental health issues among founders are common but rarely discussed.
- Startup life often requires sacrificing work-life balance for success.
- How seemingly simple problems can lead to tremendous value and growth.
- Why starting a startup isn't for everyone.

Keywords
startup stress, mental health, entrepreneurship, product-market fit, venture capital, startup journey, growth, leadership, team dynamics

Timestamps
(00:00:00) Intro
(00:01:07) The Stress of Being a Startup Founder
(00:05:42) The Responsibility for your Workers as a Founder
(00:07:27) Work Life Balance Can't Exist
(00:15:39) The Origin of Aiwyn
(00:20:30) The First Product
(00:27:46) The Main ROI and Business Model of Aiwyn
(00:30:52) Starting During the Pandemic
(00:32:14) The Seed Round & Growth
(00:37:01) Series A
(00:41:41) Reputation Matters
(00:43:42) Finding True Product Market Fit
(00:44:13) One Piece of Advice

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Rob founded Outpoint in 2020 to help marketers optimize their ad spend. He was a growth marketer and his founder a data scientist. He had team-market fit, a solid thesis, and paying customers. But when the recession hit and ad spend dropped, growth ground to a halt. Nothing he did could revitalize growth. Ultimately, he decreased expenses and exited. He was able to return some cash to investors, find a home for his team and keep the product going.

You tend to hear about what happens to the best 1% of startups. Here’s what tends to happen to the other 99%.

Keywords

Outpoint, product market fit, startup journey, acquisition, growth marketing, venture capital, business strategy, lessons learned, entrepreneurship, market dynamics

Why you should listen

• Why a great team and thesis won’t always lead to success
• How things out of your control can completely change your trajectory
• Why you should build something that works in both up and down markets
• How to find an acquisition when things aren’t going well.

Timestamps:
(00:00:00) Intro
(00:01:13) The origin of Outpoint
(00:04:40) Medium Mixed Modeling
(00:10:12) Speaking to Customers When their Revenue is Declining
(00:14:49) Outpoint's Runway in 2022
(00:19:21) Hunting to be Acquired
(00:26:07) Lessons Learned
(00:28:53) Almost Finding Product Market Fit
(00:30:23) Planning a Startup vs the Serendipity of Staring One
(00:34:30) Closing Thoughts

Send me a message to let me know what you think!