Dane was the CEO of Squarespace from 2007 to 2011. He grew the company from ~$2M in revenue to ~$15M. He's a multi-time founder with multiple exits. His current startup, Odeko,  raised $227M.He takes us through his long journey as a founder of multiple companies and shares the key startup lessons he's learned.Why you should listen:- Why 7-day trials led to higher conversion than 30-day trials at Squarespace- Why you should talk to customers every single day.- Why SMB usage doesn't always translate into revenue.- Why you need to follow customer problems over business models and TAM.Timestamps:(00:00:00) Intro(0:00:0:37) Before Odeko(00:06:54) Leaving Squarespace(00:07:31) SumAll(00:13:01) Conversion Rates with Free Trials(00:16:10) The Start of Odeko(00:20:05) Staying Close to Clients(00:26:36) Realizing the New Model was Working(00:31:47) Landing the First Few Customers(00:37:00) Overhiring(00:39:17) Finding Product Market Fit(00:41:32) One Piece of Advice

His first startup was a cool idea: Uber for Valet Parking. Investors loved it. But the unit economics didn't work out. So he had to pivot. He ended up selling it, but decided to do things differently the second time around.“It’s the boring stuff that makes money. Sometimes the sexy, interesting things are really great ideas, fun to use, but aren’t money makers. They aren’t durable businesses.”With Argyle, he didn't start with a cool idea. He replaced a product customers already paid for. His pitch went from "Wouldn't it be cool if?" to "I'll do what they do but twice as well and for half the cost"."Find a better mouse trap. Build a product that's just a better version of a product that already exists. It's a lot easier to sell." Why you should listen:- How to work with design partners to build the first version of your product- How to use those partners to get credibility and make your first enterprise sale- Keeping your sales teams small and staying close to the customer for as long as possibleTimestamps:(00:00:00) Intro(00:01:04) The Origins of Argyle(00:04:03) The Aha Moment(00:15:06) When to Charge for the Product(00:19:31)Landing the  First Customer(00:21:38) Staying Close to Customers(00:25:16) From Seed to Series A(00:32:06) Delivering clear ROI(00:35:58) Finding Product Market Fit(00:36:38) One Piece of Advice

His travel startup crashed 90% overnight. Here’s how he used AI to grow past $2M/year—to $2M a month:For a while, Andrew was crushing it. Accelerator -> $750K pre-seed -> $2M ARR -> $2.5M seed round. Then COVID hit. He was selling to events like CES, SXSW, etc.  Revenue dropped from $160K/month to under $10K... overnight. Investors from his seed round refuse to wire funds. After nearly going bankrupt, he finds a way to pivot. A year later, his business takes off.2020 - $02021 - $1M2022 - $5M2023 - $15MNow - $24M.Why you should listen:-  Andrew shares a technique to land early customers. He offered to PAY his customers to use the product.  - Learn how to deal with massive swings in revenue and unpredicted events. Early-stage founders are always one deal, one employee, one fundraise away from success... or failure.- Learn why you "can never celebrate until the money is in the bank"Timestamps:(00:00:00) Intro(00:01:16) The Start of Stay22(00:07:15) The Seed Round(00:11:53) Pivoting the go to Market(00:19:38) Investors Pulling out Due to Covid(00:26:56) Finding the Opportunity in the Pandemic(00:31:31) Tapping into the Blogger Market(00:37:31) Growing Back from Zero(00:38:49) Finding True Product Market Fit(00:39:35) One Piece of Advice

Poojan is a multi-time successful founder. He raised $60M for his first startup and exited. He just raised a $75M Series D at his current startup. But it wasn't always easy.- In his first startup, he had to hover beside conference booths for hours to land his first customer.- He gave his product away for free to the first several customers.- It took him 6 years to cross $10M in ARRWhy you should listen:- Learn exactly how a successful repeat founder thinks about team structure in the early days. Though he raised $11M, he spent only a third of it.- Understand why sometimes giving your product away for free is the best way to get off the ground.- Hear about specific sales tactics you may want to use to get your first customers.Timestamps:(00:00:00) Intro(00:01:30) Before Clumio(00:05:53)  Raising 7 Million Dollars off a Power Point(00:09:35) Starting Clumio(00:16:41) Starting Conversations with Customers(00:20:08) Finding and Solving the Real Pain Points(00:24:18) The Stage Between Series A and B(00:26:02) Keep your Team Lean(00:27:47) Finding True Product Market Fit(00:29:06) One Piece of Advice

Arvind founded 2 billion-dollar startups—by doing everything lean startup tells you not to do. - He didn’t focus on launching an MVP. - He ignored early market feedback. - He didn’t charge beta users anything—  for 2 years. And it worked. He went from $0 to $3M in revenue the year he launched publicly. He tripled to about $9M the year after. And tripled every year since. Two months ago, Glean raised $200M at a $2B valuation. Why you should listen:- Learn exactly how outlier founder Arvind Jain does things differently at the 0 to 1 stage.- Why he thinks conviction and persistence are the most important qualities founders need. - When you should follow playbooks and when to write your own.- Why it might not matter that most people don't "get" your idea in the early days.Timestamps:(2:02) Leaving Google(3:39) Coming up with Glean(7:47) Building a Product in a Neglected Space(11:38) Skipping Lean Startup(14:11) Using design partners(16:13) Building for 2 years, with 0 revenue(20:13) When it's time to launch(21:12) Why AI was a key tailwind(26:25) Finding Product Market Fit on Day One(27:32) One Piece of Advice

Snapchat got 0 downloads the day it launched. 5 months in, it had only 127 users. Today Snapchat is an $18B company with 400 million daily active users. Evan Spiegel noticed what even Zuck missed: daily communication is meant to be ephemeral, not recorded for all time.In this episode, we dive deep into how Snapchat went from idea to product-market fit. Our guest is Jeremy Liew, a Partner at Lightspeed and the first investor in Snapchat. He led Lightspeed's seed round in 2012 at a $5M valuation (!!). He shares his four-part B2C framework that helped him understand why Evan and Snap were special before anyone else. If you want to understand why Snapchat took off when so many other consumer startups fail to do so, check this episode out.

If you feel like the ‘unicorn or bust’ playbook isn’t for you, then this episode definitely will be. Rand Fishkin is a multi-time founder and published author of Lost and Founder. He founded Moz, raised $29M in VC, grew to $50M in revenue and exited for $70M. But he ultimately realized that the VC-backed life wasn’t for him. So he went on to start SparkToro, a profitable 3-person startup that does $2M in revenue and takes only 30 hours a week of work. For those of us in the VC-backed startup world, it’s a totally different way to play the game. It won’t make you a billionaire. But it very well may make you $10M— with less stress, less work, and less risk. If you want a transparent account of the pros/cons of a venture-backed vs a bootstrapped startup, check this episode out.

While Voice AI is all the rage now, it wasn't a hot sector in 2017. After Dylan graduated from YC, VCs rejected him. He couldn't raise a round. They all assumed Google would do it. So he raised what he could from angels and made it work for the next 3 years.He's now built the world's most accurate Speech AI model. He's grown to 5,000 customers and raised $115M in venture capital. Last quarter, he raised a $50M Series C from Accel. Just this week,  Assembly launched Universal-1, their most powerful speech recognition model to date. Trained on over 12.5 million hours of multilingual audio data, Universal-1 is 22% more accurate than APIs from Azure/AWS/Google and has 30% fewer hallucinations than competing models.In this episode, we go through how Dylan came up with the idea, how he saw Gen AI coming long before others, and what he did in the early days to grow to $1M in ARR.

Andrew is the founder/CEO of Enable. And he is riding a rocket ship:2020: $17M Series A2021: $45M Series B2022: $94M Series C A few months ago he raised $120M at a $1B valuation. But it took him five years from the time he started Enable in 2015 until he was able to raise his first round in 2020. Andrew was running a profitable development shop as he built the first version of Enable. He often had to chase down customers so he could make the next payroll. He had to balance serving existing customers while building an entirely new startup. Ultimately, he had to move to SF to raise a round and accelerate growth.We go through the details of how Andrew turned a 'boring' enterprise software company from the UK into one of America's hottest new unicorns.

Alex started Apt2B in 2010. He sold couches online before IKEA did. It took him over 3 years to make as much money as he used to as a furniture salesperson. But it paid off. After growing the business to $6M in revenue, he sold the company.Post-acquisition he grew the company to $40M in sales. In this episode, we dive deep into what Alex did to get started, how he closed his first few customers and what he did to grow to $1M in revenue.From landing a Super Bowl ad to selling couches at Costco, this episode is full of sales and marketing anecdotes you can steal. You don't want to miss it.Following the sale, Alex is now back at it as the founder and CEO of couch.com, a platform to help people find great furniture.

Every founder wants to build the next $1B+ company. So it’s normal to get inspired by what companies like Apple, Shopify and Microsoft do. But it’s also a huge mistake. In this episode, we look at what Shopfiy, Fullscript and Spellbook did to find product-market fit. In many ways, it’s the opposite of what they do now, as big succesful companies. Big companies are operating in a post-product-market fit world. Pre-product-market fit startups are in a different world entirely. The same rules don’t apply.

Spellbook is ChatGPT for lawyers. They've raised $30M in the last 6 months. They now have over 2,000 law firms as customers. But it wasn't a straight line-- it took Scott 6 years to get here.For the first 5 years, Scott worked on a legal tech platform called Rally. During that time,  Scott along with his co-founders and their small team ran hundreds of experiments, pushed dozens of landing pages and built a process to test feature after feature.In this episode, Scott goes through his process to test product-market fit. It was because of this process that he was able to jump on the AI-enabled opportunity and grow 12x in one year.

Kyle Braatz is the founder of Fullscript, a $900M revenue company that started by helping health practitioners recommend supplements to their patients. It's like the Shopify for doctors, nurses and nutritionistsEven though he captured 50% of the Canadian market in one year, early-stage VCs didn't see the opportunity. So he bootstrapped his way to success. He cracked open the US market and quickly scaled from $0 in 2012 to $25M in revenue by 2016.Today, Fullscript has grown to a profitable company that makes it easy for health practitioners to prescribe and manage treatment plans for whole person health, through their market-leading tech platform.If you're struggling to raise but know you have a huge opportunity ahead of you, you won't want to miss this episode.

Aydin Senkut is the Founder and Managing Partner at Felicis. He invested in Shopify's Series A in 2010 at a $25M valuation. He joins us to tell the story of how Shopify found product market fit.Shopify is now a $100B company. But as Founder & CEO Tobi Lutke said, in the early days, his goal was "to build a 20-person company". Shopify is not a story of explosive, 10x growth and massive funding rounds. Shopify is a story of consistent growth. Of doubling year after year, from 0 to over $7B in revenue and a $100B valuation.If your goal is to build a generational company,  you won't want to miss this episode.

If you've been struggling to raise—you're not alone. Seed funding has been falling every quarter for the last 2 years. Rounds are smaller and take longer to raise.So we decided to record an episode to help you. Here are all the mistakes, tips and tricks we’ve seen first-hand that actually work.  We touch on things likeWhat the perfect raise looks likeWhy Post-Money SAFEs are TERRIBLE for foundersThe greatest power move that any founder can use when fundraising If you’re raising or planning to raise anytime this year, in a macro environment that is not friendly, don’t miss this episode.

The Super Bowl is the best place to get in front of customers—if you have $10M to spend. Which means for virtually all startups, it’s 100% useless. So I decided to look into some of the best campaigns early-stage startups used to drive millions of leads. Shopify used a $100K Build A Business Competition in 2010  when it was a bootstrapped business. The campaign drove 1350 new businesses and was paid back in under a month.https://shawngraham.me/blog/shopifys-kickass-build-a-business-contestDollarShaveClub launched with a YouTube video about its $1/mo razors. The video was everything a GIlette ad was not. The company was ultimately acquired for $1B.https://www.youtube.com/watch?v=ZUG9qYTJMsI&t=1sPurple had the famous Raw Egg Goldilocks video that compared its mattress to others by seeing which one broke raw eggs. For less than $10K it got 200M views, more than the Super Bowl itself.https://www.youtube.com/watch?v=4BvwpjaGZCQ

This isn’t a unicorn fairytale. It’s a story about what it really takes to build a company and get to an exit.Nazim takes us through how he nearly went bankrupt, took years to turn things around, and ultimately sold his business for $30M all cash.

4K likes, 365 re-shares and over 1M views, without any marketing spend.  For an ad promoting your product, that sounds too good to be true-- and yet that's exactly what Yoav did.  He leveraged it to get tons of press, more customers than he could manage, and raise a $15M Series A in under a year after incorporating. Here's the story of how Yoav got started with Walnut and how he ultimately found product-market fit. Yoav goes deep on tactics you can use to drive inbound traffic, generate leads and fundraise.Viral video: https://www.linkedin.com/posts/yoav-vilner_weareprospects-weareprospects-activity-6960959679111778304-nOrW?utm_source=share&utm_medium=member_iosViral video 2: https://www.linkedin.com/posts/yoav-vilner_weareprospects-weareprospects-activity-7006660780150427648-P4vD?utm_source=share&utm_medium=member_ios

$1B startups get all the hype. But for 99% of founders, it’s the wrong goal. You’re better off building a sustainable business with consistent growth. Raising big rounds won’t make your company big and staying lean won’t make your company small.  That's just VC Myth 1. Raising round after round does not equal success. That's just VC Myth 2.Just because you raise more money, doesn’t mean you make more money. That's just VC Myth 3.

Over 10 years of hard work, Ilya has helped over 2000 individuals change their lives. In the meantime, he built a profitable, cash-flowing business with no outside funding. While the billion-dollar outcomes get all the hype, this is what success looks like for most founders. In this episode, we dive into how Ilya turned a resume-editing business into a multi-million dollar recruitment platform, how he landed his first customers, and exactly when he knew he had product-market fit.