New Carta data shows that 30% of seed-stage startups used to raise a Series A within 2 years of their seed. Now, only 15% do. The bar for Series As is as high as it's ever been. And the number of seed extensions that I see is going up as a result.

But for founders, this is NOT a bad thing. I remember as a seed-stage founder I was obsessed with raising a Series A. But now I've seen startup after startup that raised $8-12M Series A when they didn't truly have product-market fit. Most of those startups ended up hiring too many people, burning too much money, and not growing any faster. They are now money-losing startups with no growth.

The VCs aren't happy, but they're okay. But the founders aren't. They are at the bottom of the stack. They can't sell their business and can't grow it either. They're stuck between a rock and a hard place.

The solution? If you're not performing at top quartile levels, if you don't have clear undeniable product-market fit, then raise a smaller round.

Seed extensions might not be what you wanted—but in many cases, it's what you need.

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

Liran quit a cozy job at IBM to launch Fusic, a TikTok-like app back in 2011. He raised over $10M, acquired tens of thousands of users, and failed.

So he went back to what he knew: deep tech and enterprise. He launched WEKA in 2014 to improve the efficiency of GPUs. He was operating on hard mode: building deep tech and selling to large enterprise customers. It took him 5 years to build a commercially-ready product. In that time, he raised over $35M from strategic investors, since VCs didn't get it.

Once they launched, they more than doubled every year. And this year, they crossed $100M in ARR.

Here's how Liran built WEKA and got it off the ground.

Why you should listen:

• Why deep tech is much harder than normal software startups and always takes much longer.
• How to get enterprise customers to commit well before your product is ready.
• How to leverage strategic investors to get you through the early days when you have no revenue.
• How Liran was able to get customers to pay 6-figure deals when competitors offered 'similar' products for free.

Keywords
Weka, deep tech, large enterprises, GPUs, OS, product-market fit, funding, strategic investors, POCs, POVs, AI, GPU use case, performance, cost reduction, rapid growth


Timestamps:
(00:00:00) Intro
(00:02:12) Why my first startup failed
(00:08:35) Starting WEKA
(00:15:04) WEKA's First Customer
(00:17:43) The Operating System of CPUs
(00:21:19) The Issues with Deep Tech Companies
(00:26:19) Competing with a Free Product
(00:32:57) Reaching a Couple Million in ARR
(00:36:26) Fundraising
(00:43:19) Finding Product Market Fit
(00:44:08) One Piece of Advice

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This episode is going to piss you off. Most founders struggle to raise their first few million. Many have to bootstrap for years. Even once there's revenue, many get rejected because they're "too early".

Dan had dozens of VCs asking to invest before he even quit his job. He raised his first $5M with no deck, no story, and no product idea. All it took was two founders who wanted to build something in the security space. To add fuel to the fire, 6 months after he incorporated, he raised a $50M round from Sequoia... with no revenue!

He didn't pitch dozens of VCs. He didn't create a deck. He just spoke to a partner at Sequoia and had a term sheet in 3 days. The reasons are part macro, part team, part market... and part just the insanity that sometimes happens in Startup Land.

It's hard to beleive and makes little sense from the outside. But it often works. Chainguard just closed $140M Series C, has 100s of customers and does 8 figures in ARR.

Here's how it happened.

Why you should listen:

• Why launching multiple products at once worked for Dan.
• How to raise from a position of strength to get favourable terms.
• Why identifying the right markets can be such an important step.
• Why time to value and leads to fast growth and high close rates.

Keywords
startup, fundraising, product market fit, Sequoia, security, open source, venture capital, entrepreneurship, growth strategies, technology, innovation

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

It was “really slow in the first couple of years...really, really slow.” GoHenry was an app and debit card for kids to help parents teach their kids about money. Dean started over a decade ago in 2012, when mobile was just truly taking off.

And yet, it took multiple years to get off the ground. Once he found the right channels and repeatable growth, he and his team started pouring fuel on the fire. In total, they raised over $100M.

He ultimately grew to 2 million paying customers. Earlier this year, they were acquired for an undisclosed sum in what is one of the bigger fintech M&A deals of the last few years.

Here's how it happened.

Why you should listen:

• Why even with millions of paying users, Dean speaks with a handful of customers one-on-one every week.
• Why timing is so important and how to spot trends early-on based on small things happening around you.
• How finding the right channels is key for consumer startups.
• Why Focus and clarity are key to maintaining a successful business.

Keywords
GoHenry, startup, acquisition, product market fit, customer feedback, financial education, kids debit card, scaling, marketing strategy, entrepreneurship

Timestamps:
(00:00:00) Intro
(00:1:34) The Beginning of GoHenry
(00:5:57) Why I talk to users every week
(00:11:22) You Grow by Learning Faster than Your Competitors
(00:26:50) V1 of GoHenry
(00:35:26) Getting to 10,000 Customers
(00:38:33) Conversion Rates from Social Media
(00:41:51) Getting Acquired
(00:50:59) Finding Product Market Fit
(00:51:33) One Piece of Advice

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

Jaspar graduated YC & closed a $11.5M seed round this week. He launched Artisan just 8 months ago. And this is the first venture-backed startup he's ever ran.

He started with product-led-growth but struggled. In May, he moved to a sales-first go-to-market & scaled from $200K ARR to $1.3M ARR by September.

We go deep and tactical to figure out exactly what he did to grow so fast: from hiring a Chief of Staff as one of his first hires, to living in the same house as his employees, to meeting 50-100 Account Executives for each AE he hires. He shares specific numbers, specific tactics, and specific mistakes he made along the way.

Why you should listen
- How solving a #1 priority problem is the single biggest reason for fast growth.
- How to use LinkedIn, Reddit, and SEO to generate so many leads your AE's are drowning. (Jaspar's AEs do 20 demo calls per day).
- How to close yourself by hiring a Chief of Staff early on.
- How to find 10/10 Account Executives that closes $300K ARR in their first month.

Keywords
startup growth, sales strategy, marketing tactics, customer success, hiring AEs, product-led growth, sales-led growth, founder insights, business scaling, ARR, product-market fit

Timestamps
(00:00:00) Intro
(00:03:44) Getting leads from Reddit
(00:06:00) Launching V1 quickly
(00:12:28) Getting leads from blogs & SEO
(00:15:33) Getting leads from LinkedIn
(00:17:10) Why you should hire a Chief of Staff Early
(00:21:30) How to hire the best Account Executives
(00:24:46) How to get to $1M ARR
(00:26:10) Making Customers Successful
(00:29:43) One Piece of Advice

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

Cody started a ride-share business in 2017 with no capital. He focused exclusively on small towns (<100K) where Uber/Lyft weren't available. I would 100% have passed if he pitched me years ago—and I would've been dead wrong.

So far he's raised only $2.1M, compared to Uber's $30B+ raised. And yet, he build a business doing $20M+ in annual revenue that is live in a dozen markets and multiple countries.

Besides competing with massive companies, he was also weeks away from bankruptcy when ride-share froze during the early days of COVID. He goes through exactly what he did to survive—and to grow well beyond where he was pre-COVID just a year after.

If you're bootstrapping or competing with better funded players, check this episode out.

Why you should listen:

• Why even massive competitors often don't mean you can't build a business.
• How to hack your way to millions in revenue with no budget.
• Why customer service and success are the keys to unlock word-of-mouth.
• How to survive 3 weeks of cash and near-bankruptcy.

Keywords
Uride, rideshare, entrepreneurship, bankruptcy, business growth, startup challenges, market expansion


Timestamps:
(00:00:00) Intro
(00:01:48) Thunder Bay Ridesharing
(00:03:49) A Problem that Shouldn't Exist
(00:06:44) The Launch
(00:08:15) Growing and Outgrowing
(00:10:50) A Bylaw Loophole
(00:13:27) Expanding to Other Communities
(00:17:05) Three Phases
(00:21:54) Surviving
(00:29:18) The Demand Curse of Ride Sharing
(00:34:09) Unride Focus
(00:39:46) Long Ways to Go

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I tried to pay my employees as little as possible. I thought I was being resourceful—& it seemed to work. Until it totally backfired. I learned my lesson the hard way.

No founder wants to hire B-level or C-level talent. Everyone is looking for A-players. But most founders don't put in the work. And they end up with B-level teams.

If you're serious about getting and keeping A-players there's only one way to do it. You need to have a coherent strategy, you need to be intentional, and you need to make it priority number one. Here's how.

Takeaways

• Why paying employees less than they're worth incentivizes the wrong behaviour
• Why you need to have a system for regular performance reviews and salary adjustments.
• How to attract and retain A players
• How great junior talent can outperform B-level experienced talent.

Keywords
founders, compensation, hiring, A players, salary strategy, employee retention, startup culture, leadership, team building, performance reviews

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

Kyle left his job as a hacker at the NSA to launch Huntress. He bootstrapped for 3 years and burned all his savings. One of his co-founders quit. He got into an accelerator program, but had to sleep in his car for 16 weeks because he couldn't afford a hotel.

Finally, 3 years in he'd hit $1.5M ARR. So he pitched 60 VCs for a Series A—and got 60 'no's. He was forced to raise a small, $1M inside round.

But then things changed:

2018: $1.5M ARR
2019: $5M ARR
2020: $10M ARR
2021: $20M ARR
2022: $40M ARR
2023: $70M ARR
2024: $100M+ ARR

Huntress is valued at $2B.

The investors who backed his $1M bridge are up 140x.

Now every VC wants to invest—and Kyle's the one saying 'no'.

Why you should listen:

• How to know whether you should keep going or quit.
• What it takes to get through the first few years at a bootstrapped startup.
• Why revenue expansion is a huge lever for fast-growth (Huntress has 140% net revenue retention).
• How starting a startup can impact your personal life and relationships.
• How to work with partners to sell to long tail SMB customers.

Keywords
entrepreneurship, cybersecurity, product market fit, startup journey, military experience, SMB market, funding challenges, automation, human expertise, business growth

Timestamps:
(00:00:00) Intro
(00:2:01) Working at the NSA
(00:6:14) A big win in counter cyber terrorism
(00:10:00) What gave way to Huntress
(00:14:22) Pitching to a startup accelerator
(00:16:29) Adopting curiosity
(00:21:04) Getting ahead of cyber criminals
(00:26:00) Starting to grow
(00:32:50) Cult or conviction
(00:35:00) It takes grit
(00:39:50) Learning from people's lessons
(00:42:20) Cockroaches and underdogs
(00:46:10) Three strikes, I'm out
(00:52:56) Having a military background
(00:56:17) One piece of advice

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