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

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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

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Cameo is one of the best-known recent consumer startups. You've either used it or know someone who's used it to get famous people to create personalized videos. And, for a while, they were a total rocket ship.

Year 1: $300K GMV
Year 2: $4M
Year 3: $20M
Year 4: $100M

They were backed by Jeremy Liew, the VC who seeded Snapchat in 2012. Cameo became a unicorn in 2021. But as the markets turned, revenue decreased, investor interest waned, and their valuation dropped from $1B to $100M. After the restructuring and the layoffs, Steven found a way to turn things around.

Now the company is profitable again. And growing.

Here's how he did it.

Why you should listen:

• Why you don't need liquidity to launch a marketplace.
• How to hack your way to a successful marketplace launch.
• Why organic growth is the way to grow a marketplace.
• How to turn things around after your valuation crashes by 90%.

Keywords
Cameo, startup, entrepreneurship, product-market fit, celebrity endorsements, marketplace growth, business strategy, VC funding, early-stage startups, innovation, Cameo, gifting, unicorn status, Chicago startup, engagement, COVID-19 impact, business diversification, down rounds, product-market fit

Timestamps:
(00:00:00) Intro
(00:02:46) Where The Idea for Cameo Came From
(00:11:54) The Client Interface of Cameo in the Early Days
(00:14:12) The Failed launch that Could've Ended it All
(00:21:23) Gaining Momentum
(00:25:37) The Math Behind Cameo
(00:31:27) Becoming a Unicorn
(00:34:34) Meeting Jeremy Liew (the VC who backed Snapchat)
(00:40:47) Engagement on the Platform
(00:43:00) The Impact of Covid
(00:56:06) Finding Product Market Fit
(00:56:30) One Piece of Advice

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Q3 startup data just dropped. We chat with Peter Walker, Head of Insights at Carta about valuations at pre-seed, seed and Series A. Why the current fundraising environment is the new normal and not about to get much better. We also talk about trends in founder vesting, and why some founders are choosing to vest for longer.

Finally, we go through what to do if you’re stuck with some product-market fit but mediocre growth, and why more exits are happening now than anytime in the fast couple of years.

Why you should listen

• Founders should not expect a return to the fundraising conditions of 2021.
• Competition among founders has increased, raising the bar for fundraising.
• Many startups are still alive despite challenging conditions, adapting to survive.
• Why the professionalization of the startup ecosystem offers more options for founders.
• Startup ecosystems are growing in tier two and three cities.
• What the one-and-done funding model is and how to use it.

Keywords
State of private markets, early stage funding, SAFEs, startup trends, liquidity, valuations, venture capital, market analysis, fundraising, AI, AI startups, vesting schedules, funding models, startup ecosystems, venture capital

Timestamps
(00:00:00) Intro
(00:01:33) Top Highlights from Q3 Report
(00:04:45) The market won't get any easier
(00:06:13) Two Reasons why the SAFE Boom Could Change Things
(00:12:34) Professionalization of the Industry is a Double Edged Sword
(00:17:44) Rounds that are Leading the Market are as Competitive as Ever
(00:22:36) Vesting Schedules
(00:30:05) Best Location to Raise & the One and Done Method

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Lior is the Elon Musk of VC. In just 8 years, his venture fund went from 0 to $4B under management. And while doing that, he founded Bright Machines, which to date has raised over $400M. He's both the CEO of Bright Machines and the Managing Director of Eclipse Ventures.

And he's not building "easy" software startups either. Bright Machines is looking to automate the entire manufacturing process with robots. He launched it with a $179M round and a 100-person team.

Lior is not normal. His story isn't either. You won't want to miss this one.

Keywords
venture capital, startup journey, Bright Machines, manufacturing innovation, fundraising challenges, robotics, automation, customer relationships, product market fit, entrepreneurship, Eclipse Ventures

Timestamps:
(00:00:00) Intro
(00:08:31) Starting Eclipse & Becoming a VC
(00:13:58) How he started Bright Machines
(00:18:43) The First enterprise deal with Flextonics
(00:24:49) The Process of Automation and Assembly
(00:30:25) Making a Machine as Reliable as a Human
(00:34:44) Bright Machine's Struggles
(00:36:56) The Business Model of Robotics
(00:39:49) Finding Product Market Fit
(00:40:37) One Piece of Advice

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Parker quit his job as VP Finance at a late-stage startup in mid 2021. He raised $4M out of the gate because, well, it was 2021. But he didn't ramp up sales, he didn't hire 15 developers. He kept the team to 5 people for the first year.

He worked with a dozen design partners until the value prop was perfect. He even refused to let customers pay upfront in annual contracts. He wanted monthly payments to light a fire for him and his team.

This month, just 3 years after quitting his job, he closed a $28M Series A.

Here's exactly how he did it.

Why you should listen:

• Why the early stages are all about customer value and delight.
• Why you need to focus on product-market fit before growth.
• Why you need to solve a top-of-mind problem and deliver clear ROI to take off.
• How to transition from build mode to sales mode.
• Why monthly contracts can provide valuable feedback loops for early-stage startups.

Keywords
Numeric, startup, product-market fit, funding, accounting, customer engagement, sales strategy, ROI, growth, Series A

Timestamps
(00:00:00) Intro
(00:01:07) Coming Up with the Idea
(00:06:13) Research, Taking the Leap & Pre-Seed Funding
(00:11:48) Keeping the Team Small
(00:16:55) Why Annual Payments Don't Work Early On
(00:22:10) The Challenges in Going into Market
(00:26:53) Measuring ROI
(00:33:26) Series A
(00:35:05) Finding Product Market Fit
(00:36:11) One Piece of Advice

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Mike started selling SaaS before SaaS was a thing. PointClickCare is the Salesforce of healthcare. For the first 7 years, they raised just $600K from friends and family. With that funding, they grew to $50M in ARR.

Through that time, they went through the 2000 Dotcom crash and nearly went bankrupt in 2004 as they chased too many markets too soon.

Since then, the company has continued to grow at over 20% compounded rate and hit $500M in ARR in 2024 and a $5B valuation.

Mike shares how they started the company, the go-to-market strategy they used to go from 0 to $10M ARR and some of the most common mistakes he sees in the founders he works with today.

Why you should listen:

• Why you might need to live with your customers to really understand them.
• Why the first 10% market share is the hardest to achieve.
• How chasing the wrong sales opportunities can lead to customer disappointment.
• Why you need to focus on delighting customers before chasing revenue.
• Why TAM isn't nearly as important as founders are made to think.

Keywords
product market fit, startup growth, healthcare technology, customer delight, market entry, capital efficiency, company culture, founder advice

Timestamps:
(00:00:00) Intro
(00:01:43) Target Market is as Important as PMF
(00:06:42) The Origin of PointClickCare
(00:10:23) Being a Pioneer in SaaS
(00:20:18) Measuring Customer Delight
(00:28:40) Common Mistakes when Trying to Find PMF
(00:34:32) Entering the US Market
(00:37:57) Surviving Payroll to Payroll
(00:40:13) Losing the Original Ethos of your Company
(00:52:08) Finding Product Market Fit
(00:53:48) One Piece of Advice

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