Explore every episode of the podcast A Product Market Fit Show | Startup Podcast for Founders
Dive into the complete episode list for A Product Market Fit Show | Startup Podcast for Founders. Each episode is cataloged with detailed descriptions, making it easy to find and explore specific topics. Keep track of all episodes from your favorite podcast and never miss a moment of insightful content.
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Title
Pub. Date
Duration
He made 2 key changes —then grew to $100M ARR in 2 years & exited for $2B. | Harish Abbott, Founder of Deliverr & Augment
06 Nov 2025
00:52:12
Harish spent 9 months building Deliver and could barely get 10 customers. The product worked. Merchants liked the fast delivery promise. But nobody was signing up.
Then he made two changes—and scaled to $100M in revenue in 2 years. Shopify acquired them for over $2B.
Harish says it wasn't about finding product-market fit. It was about finding product-PRICE-market fit. The product was fine. The pricing model was killing them.
This episode breaks down why pricing often isn't just a business decision—it's part of your product, how to build self-serve systems that scale to thousands of customers without talking to anyone, and why you must obsess about end users AND economic buyers if you actually want adoption.
Harish is now building Augment, an AI company for logistics that just raised an $85M Series A. He shares what he learned shadow-sitting operators for 60 days and why demos mean nothing in the AI era.
Why You Should Listen:
Why PMF is often not enough—you need product-price-market fit
Why subtle changes can have huge results
Why you need both users AND buyers to love your product
00:00:00 Intro 00:07:06 Starting Deliver in 2017 00:14:24 Struggling with only 10 customers after 9 months 00:19:53 The two changes that changed everything 00:23:43 Zero to $100M in 2 years and product-price-market fit 00:29:32 How the $2B+ Shopify acquisition happened 00:32:07 Starting Augment AI for logistics 00:47:35 PMF moments and top advice
He built a $20B public company, left—then raised a $100M Series A. | Dheeraj Pandey, Founder of Nutanix & DevRev
03 Nov 2025
00:49:07
Dheeraj built Nutanix into a $20B public company—then walked away to start DevRev. He just raised a $100M Series A.
This episode breaks down why most founders "sell and run" (chase new logos instead of delivering value), why that strategy fails, and how Dheeraj thinks about building platforms with use cases instead of just features. He explains why the biggest opportunities come from bundling and why you need to hit 130%+ NRR to scale in B2B.
Dheeraj also shares the two near-death experiences at Nutanix in the first 5 years, how they survived, and what he's building differently at DevRev in the AI-native world.
If you're wondering whether you have real PMF, how to think about platforms vs features, or why your existing customers matter more than new ones—this is mandatory listening from someone who's done it twice at massive scale.
Why You Should Listen:
Learn why PMF at $1M doesn't mean PMF at $10M—and why you have to find it again at every milestone
Why "sell and run" kills startups—the real work starts after you close the deal
See how platform thinking (not feature thinking) took Nutanix to $1B ARR
Understand why 30-40% of revenue from existing customers is real PMF
Keywords:
startup podcast, startup podcast for founders, product market fit, platform thinking, Nutanix founder, enterprise SaaS, net dollar retention, PMF milestones, fastest to $1B, second-time founder
00:00:00 Intro 00:01:58 Starting Nutanix 00:14:24 Why he left a $20B company 00:18:53 The DevRev thesis 00:27:39 Pre-AI vs post-AI product strategy and the agent shift 00:40:57 Platform vs features 00:46:25 PMF is not a destination 00:48:10 #1 Advice
A drug dealer threatened to kill him—then he grew 50x in 3 Years to $50M ARR. | Brett Carlson, Found of ServiceUp
02 Oct 2025
00:33:28
Brett had a drug dealer's car for 13 days. By day 11, the death threats started coming. This is the reality of building ServiceUp, the "DoorDash for auto repair."
Brett literally stole DoorDash's entire playbook—city launches, three-sided marketplace, everything—but discovered even if he got 90% right, 10% of B2C customers can end you.
He raised from Tiger just as the firm exploded. The DoorDash partnership that seemed like salvation turned into their worst nightmare. But then they pivoted to B2B and saw their average order value grow 5x overnight.
"Work-life balance is BS. If you can work seven days a week, you'll fail faster, fix faster, and find product-market fit faster."
Why You Should Listen:
Why just 10% of your customers can destroy your business
How to close funding in the middle of a macro crisis
Why work-life balance is BS if you want to build something big
How stealing another startup's playbook can lead to 5000% growth
Why your worst customers might actually show you your best pivot
He raised $16M, hit $1M ARR—& failed. Here are the top 3 lessons he learned. | David Anderson, Founder of Tandym
21 Nov 2024
00:54:13
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
He sold his 1st startup for 8 figures, grew his 2nd to $3M in a year—while battling panic attacks from the pressure. | Justin Adams, Founder of Aiwyn
18 Nov 2024
00:46:00
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.
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
He raised $1.5M, hit $400K ARR in 9 months— but had to Exit Early. Here’s the top 3 lessons he learned | Rob Palumbo, Co-Founder of Outpoint
14 Nov 2024
00:39:08
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%.
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 (00:14:49) Outpoint's Runway in 2022 (00:19:21) Trying to sell your company (00:26:07) Lessons Learned (00:28:53) Almost Finding Product Market Fit (00:30:23) Planning a Startup vs starting one organically (00:34:30) Closing Thoughts
His startup Cameo was a unicorn—until it crashed 90%. Here's how he went from near-bankrupt to profitable again. | Steven Galanis, Founder of Cameo
12 Nov 2024
00:57:47
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
VC funding is not popping back. THIS is the new normal—here's how to adjust. | Peter Walker, Head of Insights at Carta
08 Nov 2024
00:41:57
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
His robotics startup raised $400M, his VC fund over $4B—& he ran both at the same time. Here's how he did it.| Lior Susan, Bright Machines & Eclipse Ventures
04 Nov 2024
00:42:59
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.
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
This 1st-time founder raised $4M, kept the team to 5 people—& just raised a $28M Series A. | Parker Gilbert, Co-Founder of Numeric
31 Oct 2024
00:37:39
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
In 2004, they "almost bankrupted themselves". In 2024, they hit $500M ARR & a $5B valuation. | Mike Wessinger, Co-Founder of PointClickCare
28 Oct 2024
00:55:13
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
The top 3 reasons why Zuck is killing Apple in the Mixed Reality race.
24 Oct 2024
00:11:27
Apple sold only 370,000 VisionPro headsets-- much fewer than it expected. Meanwhile, Meta Ray-Bans are the top-selling product in 60% of Ray-Ban stores. The outcome of their AR/VR products couldn't be more different, even though they both have as much awareness as you could possible buy.
There are 3 reasons:
1. Price. 2. Killer feature vs cool product. 3. Destination vs always-on.
Check this episode out if you want to understand the where mixed reality is going and what you need to do to make sure your product takes off.
His influencer marketplace hit $150M in revenue—& just exited for $500M. It all started with a party at Coachella. | Piotr Tomasik, Co-Founder of Influential
21 Oct 2024
00:40:49
Piotr met his co-founders at a party in Coachella. He built them an app for influencers to post online. That simple idea evolved into one of the world's first influencer marketplaces.
While so many other tried and failed, Piotr and his team targeted marketing agencies with big budgets. They grew to $150M in revenue over a 10 year period. This summer, they were acquired by Publicis Groupe for $500M.
This is the story of how it all started, where the idea came from and how partnering with IBM of all companies drastically changed Influential's trajectory. Piotr also goes through in depth what it feels like to actually sell your company, and to go from living like a salaried employee to having tens of millions of dollars.
Why you should listen:
Why the right go-to-market channel is the difference between failure and a $500M exit.
How to shift from a manual process to a tech-enabled marketplace
How to know which partnerships are key— and which are totally useless.
What it feels like to go from a regular person to having $10s of millions in the bank.
Keywords
Influencer marketing, startup journey, product-market fit, technology, partnerships, exit strategy, ad agencies, growth strategies, entrepreneurship, venture capital
Timestamps: (00:00:00) Intro (00:01:27) The Start of Influential (00:11:49) Raising the Seed Round (00:14:41) How to leverage a partnership with a large incumbent (00:21:26) Series A and Superbowl Campaign (00:30:02) Winning because of go-to-market (00:35:43) The Acquisition (00:38:56) One Piece of Advice
He pitched 100 VC and spent 3 years building— then grew to $7B AUM. | Doug Scott, Founder of Ethic
29 Sep 2025
00:45:14
Doug Scott and the Ethic team spent years building technology before landing real customers. While other startups were growing fast, Ethic was focused on building, and after two years had only a modest amount of AUM. Until he and his team found a way to help his customers help them WIN new clients they couldn't land before.
That shift took them to ~$250M AUM in one year. He reveals why he left investment banking in Australia, sold everything, and moved to the Bay Area within three weeks with no idea what company to start.
He pitched over 100 investors to raise early rounds, survived years of building with no traction, and discovered the enterprise sales playbook that unlocked distribution in wealth management. Today Ethic manages $7 Billion and has raised over $160 Million in funding.
"If I knew how difficult it would be, maybe I wouldn't have done it." This is the reality of building a decade-long overnight success.
Why You Should Listen:
Why helping customers win new business is the killer ROI
How to survive a 3-year build phase when everyone else is growing fast
Why you should pitch 100+ investors even if only 5 will say yes
How to figure out distribution and go-to-market
Why the best value-add investors never pitch their value-add
Keywords:
startup podcast, startup podcast for founders, Ethic, Douglas Scott, wealth management, ESG investing, fintech, B2B2C, Series A, distribution strategy
00:00:00 Intro
00:01:47 What Ethic does
00:08:15 Leaving Australia for Bay Area with no plan
Your odds of raising a Series A just dropped from 30% to 15%—here's what to do about it:
17 Oct 2024
00:12:38
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.
His 1st startup failed—but his 2nd one hit $100M ARR & a $1.6B valuation. Here's what he learned. | Liran Zvibel, Founder of WEKA
14 Oct 2024
00:46:44
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 2013 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
He quit Google with no startup idea, raised $50M from Sequoia with no revenue— & grew to 8 figures in ARR. | Dan Lorenc, Founder of Chainguard
11 Oct 2024
00:31:48
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.
He founded a banking app for kids 10 years ago, grew to 2M customers & exited—in one of the biggest fintech M&A deals ever. | Dean Brauer, Founder of GoHenry
07 Oct 2024
00:52:52
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.
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
1st-time AI founder grows from $0 to $1.3M ARR in 8 months. Here's exactly how he did it. | Jaspar Carmichael-Jack, Founder of Artisan
03 Oct 2024
00:31:43
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.
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
He launched an Uber competitor with just $3,000—& grew to $20M in revenue in 7 years. | Cody Ruberto, Founder of Uride
30 Sep 2024
00:40:53
Cody started a ride-share business in 2017 with no capital. He focused exclusively on small towns (population <100K) where Uber/Lyft weren't available. I know as a VC I would've passed if he'd pitched me when he started—and I would've been dead wrong.
So far he's raised only $2.1M, compared to Uber's $30B+ raised. And yet, he built a business doing $20M+ in annual revenue that is live in a dozen markets and multiple countries.
At one point, he came 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.
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
The ONLY guaranteed way to attract & retain A-players.
26 Sep 2024
00:11:11
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
He got rejected by 60 VCs, burned all his savings—then grew to $100M ARR & a $2B valuation. | Kyle Hanslovan, Founder of Huntress
23 Sep 2024
00:58:31
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.
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
Forget Founder Mode— MrBeast Mode is Where it's At. | The top 7 highlights from MrBeast's leaked framework.
19 Sep 2024
00:13:03
MrBeast's 36-page framework leaked this week. It's how he built a $1B+ company and became the #1 YouTuber in the world. His channel is worth over $1B. For the first time ever, we get to see how MrBeast operates.
We go through the 7 most important things that startup founders can learn from MrBeast. From what maniacal obsession looks like, what it means to be an "A player", to how to teach employees to never take 'no' for an answer. In the leaked document called "How to Succeed at MrBeast Productions, he goes into specific details and share clear examples of what you should do.
Obsession is crucial for success in content creation.
Extreme ownership leads to better accountability.
Consultants can save time and provide valuable insights.
Persistence is key; never take no for an answer.
Every employee should know the company's expectations.
A strong culture is built on shared values and principles.
Timestamps (00:00:00) Intro (00:00:42) 1. Have a clear mission (00:02:05) 2. Hire A players (00:03:49) 3. Be Obsessed (00:05:22) 4. Extreme Ownership (00:07:19) 5. Copy & Steal (00:09:29) 6. Never take 'no' for an answer (00:010:49) 7. Write a doc!
He took on Uber & grew Rappi to $5B—here’s why the craziest founders often win. | Andres Bilbao, Co-Founder of Rappi
16 Sep 2024
00:52:56
Andres Bilboa is one of the co-founders of Rappi, the highest-valued app of LATAM ($5B valuation). Now he runs an incubator called Makers and has invested in dozens of startups.
In this episode, he shares how Rappi started with no funding and no network. They added restaurants into their platform without permission and gave cash to couriers to buy meals. Demand was through the roof. But just as they started closing funding and scaling, Uber and UberEats came to compete.
Here's the story of how Rappi found product market fit, and what Andres learned about founder psychology and mental health.
Why you should listen
How to launch an MVP even if that means giving cash to couriers.
How to fight off massive competitors like Uber and UberEats.
Why founders with insane ambition and a relentless drive are more likely to achieve outsized returns.
How the psychological aspects of entrepreneurship, such as fear of failure and the need for constant achievement, can impact a founder's well-being.
Keywords Rappi, on-demand delivery, competition, growth, fundraising, founders, ambition, drive, entrepreneurship, fear of failure, achievement, therapy, fundraising
Timestamps: (00:00:00) Intro (00:02:53) The Origin of Rappi (00:06:58) How Rappi Works (00:13:37) RappiCash (00:15:55) Colombia's World Class Convenience (00:18:05) It's a Winner Takes All Market (00:20:44) Andres' Roles at Rappi (00:22:27) Competing with Uber (00:26:00) Crazy Doesn't Cut It (00:29:51) The Problem is You are What You Achieve but Nothing Is Ever Enough (00:40:44) Fear is Unproductive (00:45:25) What is Makers (00:50:30) One Piece of Advice
PMF Observations: Speed is the only startup moat—& why most founders lose it.
25 Sep 2025
00:11:01
Arnold Schwarzenegger mastered three completely different fields—bodybuilding, acting, and politics—with one simple philosophy: reps, reps, reps. This solo episode reveals why speed of execution is the only real moat for early-stage founders.
One founder takes an idea from conception to signed customers in three weeks. Another takes six months. They both had equally good ideas, but one got 100 reps in a year while the other got 10. Even Twitter, an established app, became top 5 in the App Store not through one or two big changes but 300 small iterations.
Teams naturally slow down over time. You used to ship in days, now it takes months. You have more engineers but move slower. This episode breaks down why this happens and how to maintain that day-one velocity even at $10M ARR.
Why You Should Listen:
Why speed is the only moat early-stage founders actually have
How to get 100 reps while your competitor gets 10
Why MVPs shouldn't stop after you have a product in market
How Twitter went top 5 in the App Store with 300 tiny changes
How to Get Free PR for Your Startup—Tips from the Editor-in-Chief of Canada’s TechCrunch. | Douglas Soltys, Editor-in-Chief of Betakit
12 Sep 2024
00:46:37
Douglas has been in media and PR for over two decades. He’s the founder of Betakit Inc and has been running Betakit, Canada’s TechCrunch, for nearly 10 years. He understands what startups need to do to leverage PR, and how PR can help startups hire, fundraise and sell.
On this episode, we get tactical and go deep on exactly when it makes sense to use PR and how founders can get the most from it.
Why you should listen
Why you should treat PR like a subset of inbound marketing
PR is all about telling the right stories to the right audiences
How to conduct media profiling to find the right journalists in the right channels so you can get other people to write about you
Keywords
PR, media strategies, startups, business goals, target audiences, media storytelling, marketing initiatives, traction, leads, stories, funding announcements, product launches, media profiling, channels, audiences, founder, pitch, media, framing, storytelling, target audience, channels, journalists, PR, origin story, company values, thought leadership, customer stories, employee stories
Timestamps: (00:00:00) Intro (00:05:19) The 101 of Media PR (00:06:04) Three Questions (00:08:40) An Operational Lens for Media Engagement (00:12:16) Understanding the Target Audience (00:19:55) Inbound Marketing (00:25:20) A Super Important Caveat (00:29:08) Roam Auto as an Example (00:34:00) The Right Channel (00:36:40) Treating Media Pitching Like Investor Pitching (00:43:04) Be Professionally Interested (00:44:49) Putting a Human Face on Your Company
He built Cohere into a $5.5B AI startup; How to Win in AI; & Why LLMs won't lead to AGI. | Nick Frosst, Co-Founder of Cohere
09 Sep 2024
00:46:42
In this episode, I sit down with Nick Frosst, Co-Founder of Cohere, the $5.5B AI startup that’s targeting the enterprise landscape.
We go through the origin story of Cohere, the challenges of building foundational models, and why he believes large language models (LLMs) won’t lead to artificial general intelligence (AGI). We also explore the fierce competition in AI, what sets Cohere apart, and Nick’s advice for founders building in AI today.
Why you should listen
LLMs are powerful but have clear limitations and won't lead to AGI.
Why AI startups need to start with real problems vs leveraging AI for its own sake
Why ChatGPT was as much of a UI/UX revolution than a technological one
What tech founders need to do to win in AI
Timestamps:
(00:00:00) Intro (00:03:21) AI Expectations (00:06:05) A Unique and New Moment (00:09:38) Resource Intensive Industry (00:12:03) Zero to One (00:15:07) Base Language Model to Chat Model (00:17:15) Carving Out a Niche (00:21:03) Open Source (00:24:00) The Limits of LLMs (00:26:18) Agents (00:29:30) AGI (00:34:04) A Little Bit of Data (00:39:05) Speed of Development (00:40:47) Finding True Product Market Fit (00:43:37) One Piece of Advice
The ONLY guaranteed way to find Product Market Fit
05 Sep 2024
00:16:08
Even if founders do everything right, they may still fail to find PMF. That's why even repeat founders have only 1.5% chance of building a unicorn.
We talk about product-market fit constantly in this podcast. Hopefully, we learn from what others did and improve our chances of finding PMF. But there is only one way to guarantee that one day you will find product market fit. We explore that in this episode.
**Got sick this week so re-releasing one of the most downloaded short episodes from last season that was originally published exactly a year ago today.**
They hit $100M ARR—in a "crowded market". Here's how they got to $1M ARR in just 18 months. | Don Mal, Co-Founder of Vena Solutions
03 Sep 2024
00:40:42
Don co-founded Vena & was CEO for 8 years. Last month, Vena became a Centaur crossing $100M in ARR.
Don & his team launched Vena in a crowded market, where everyone else was trying to replace excel. So they built a budgeting and planning (FP&A) solution that instead leveraged excel. As Don says, they "disrupted the disruptors".
Don knew the problem, he knew the space, he knew the customers— that’s why he grew from 0 to $1M in ARR in 18 months.
Here's exactly how he did it.
Why you should listen
How to close the first few customers
How to close 6-figure deals without any proof points
Having knowledge and a network in the industry you're entering makes it easier to find success as a founder.
In crowded markets, a differentiated approach and the ability to solve pain points for customers are key to standing out.
Why there's no feeling like the satisfaction of taking an idea and product to market, working with great people, and seeing others succeed.
Timestamps: (00:00:00) Intro (00:02:36) The Beginning of Vena Solutions (00:06:06) Step 1 of Vena (00:09:35) First Conversations (00:11:09)The Market in Planning (00:17:50) The Market in Workflow (00:20:02) Wealth Fargo (00:22:23) Getting to a Million (00:26:05) The Biggest ROI (00:29:03) Una (00:34:33) Not Retiring (00:35:55) Finding Product Market Fit (00:38:29)One Piece of Advice
This founder was hours from hiring a VP Product—turns out, he was a total fraud. Here’s what he learned.
29 Aug 2024
00:10:48
It's the first time I see a candidate BS his way through interviews with multiple people, impress each one of them, and ultimately end up being a complete fraud. But the biggest learning wasn't that you should watch out for fraud-- it was that you shouldn't trust interviews nearly as much as you'd think.
While fake candidates are rare, candidates who are 10x better at interviewing than they are at the job are quite common. In fact, the only thing you know about candidates with great logos is that they know how to interview. Otherwise, they wouldn't have worked at Google in the first place.
What you don't know is if they're truly great. Here's how to find out.
Takeaways
Don't rely solely on interviews when hiring
Hire based on referrals and conduct thorough reference checks
Former founders are often the best hires
Logos and impressive resumes don't mean as much as you think
He quit his cozy Google job & founded not 1 but 2 unicorns— then grew from $1M to $12M ARR in 2 years. | Ashutosh Garg, Founder of Eightfold AI
26 Aug 2024
00:36:22
Ashutosh is one of those rare founders who founded not just one, but two unicorns. He worked at Google for 4 years, left and started Bloomreach, which was last valued at $2.2B.
Halfway through that journey, he left to do it all over again. He started Eightfold AI which is the one we're talking about today. In 2021, he raised $220M from Softbank at a $2.1B valuation.
When he left Bloomreach, he didn't even have a clear idea of what he was going to build. He just knew he wanted to have more impact and go from 0 to 1 again.
It took him about 2 years to figure it out— then he grew from $1M ARR to $3M ARR in a year & to $12M ARR the year after that.
Why you should listen
Why founders need to validate ideas with an open mind to not have tunnel vision.
Why even unicorn founders don't get it right and often need to pivot to success.
How to address problems that are not just today problems, but likely to be problems for a long time.
Keywords
unicorn founder, Bloomreach, Eightfold, product-market fit, pivot, HR space, digital marketers, talent, hiring, market need, scaling
Timestamps: (00:00:00) Intro (00:01:41) His first unicorn - Bloomreach (00:05:22) Starting Eightfold AI (00:08:50) Not Marrying Yourself to One Idea (00:11:55) Finding real customer problems (00:14:46) Solving Today's Problems vs Future Problems (00:16:47) Hiring From Already Rejected Candidates (00:22:50) Fundraising (00:24:40) Building a V1 (00:27:00) Pivoting and then Reverting Back (00:30:43) First Customers (00:32:59) Finding Product Market Fit (00:35:04) One Piece of Advice
Q2 Early-Stage Venture Report w/ Carta’s Head of Insights: Valuations, Round Sizes, Graduation Rates & more. | Peter Walker, Head of Insights at Carta
22 Aug 2024
00:40:39
Carta is the backbone of most venture-backed startups. They have access to specific information about every single round, not just what's reported in TechCrunch.
Today, Peter Walker, Carta's Head of Insights joins us to share the findings from Carta's Q2 reports. We go deep into data from pre-seed, seed and Series A rounds. We cover median valuations, time between rounds, graduation rates between rounds, the AI and repeat-founder premiums, and much more.
VCs know most of this data. Founders need to be equally well-informed. You won't want to miss this episode.
Why you should listen:
What are the typical pre-seed, seed and Series A rounds.
Why stacking SAFEs is very dangerous.
How to minimize dilution in the early-stages
What is standard founder ownership, founder equity splits and ESOP sizes.
Why the graduation from Seed to Series A is so low and the bar for Series A so high.
Many more data points for pre-seed to Series A Venture Capital and Startup data.
Keywords
startup ecosystem, fundraising trends, total fundraising, down rounds, bridge rounds, company shutdowns, pre-seed funding, seed funding, series A funding, valuations, round sizes, dilution, founder equity, early employees, equity compensation, seed round size, series A
Timestamps: (00:00:00) Intro (00:01:35)Findings from the Q2 Report (00:06:12)Typical Pre-Seed Round (00:07:29) Post Money Safe vs Pre-Money Safe (00:11:54) AI and Repeat Founder Premiums (00:15:03) Typical Seed Round (00:17:07) Time & Graduation Rates Between Rounds (00:22:08) Typical Series A (00:28:14) Equity Splits (00:35:02) Founder Ownership
He built in stealth with 1 customer for a year—then grew to 1M paid users across 60,000 locations. | Sanish Mondkar, Founder of Legion
19 Aug 2024
00:42:21
Last quarter, Sanish raised a $50M Series D. His company has raised over $130M. They have enterprise customers across 14 countries including Dollar General, Aldo, and CircleK.
It all started because Sanish was working out of coffee shops. He wasn't looking for a startup idea. But after a few casual conversations with employees, he noticed several problems retail workers and managers faced. He decided to build Legion to solve them.
He partnered with one local coffee chain, worked as a barista for a week, and developed the product with them for a year. He didn't sell to other customers, he stayed heads down until the local chain adopted the product across their entire organization. By the time they went to sell to other enterprises, they knew the product worked.
Why you should listen
Why listening with an open mind is a common way to identify customer problems.
Why providing clear and immediate ROI is a must-have for enterprise customers
How to perfect your product with design partners that are heavily invested
How to raise a Series A without meaningful revenue.
Keywords
Legion, workforce management, enterprise software, problem validation, value proposition, scaling, pricing model, ROI
Timestamps: (00:00:00) Intro (00:01:35) The Origin Story of Legion (00:04:53) The Mindset of Most Frontline Workers (00:11:05) Gathering Data (00:20:00) Building an MVP (00:24:30) Insights from Customers Using V1 Products (00:30:15) Series A (00:32:13) Legions Core ROI (00:36:15) Scaling Legion (00:39:47) Finding Product Market Fit (00:41:19) One Piece of Advice
Sean Ellis led growth at Dropbox—& invented growth hacking. Here's his step-by-step growth guide. | Sean Ellis, creator of the PMF test & best-selling author of Hacking Growth.
15 Aug 2024
00:47:07
Sean Ellis created THE test for PMF. He led growth teams at Dropbox, Eventbrite and LogMeIn, which sold for $4.3B. He coined the term Growth Hacking and wrote the best-selling book Hacking Growth.
Today we go deep and tactical with him. He takes us through how to use the Sean Ellis test to perfectly measure and understand product market fit.
He takes us to case studies of things that he did at LogMeIn and Dropbox to dramatically increase growth. And he shares exactly what you can do to drive more referrals for your startup.
Why you should listen:
Why the Sean Ellis test is THE product-market fit test every founder should use. How to implement it today and use it to get closer to PMF.
Why a great first-time user experience is the key for growth and referrals.
How to optimize each growth levers, such as acquisition, activation, engagement, retention, and referrals.
How to build a data-driven culture that is focused on measuring and improving PMF.
Keywords product-market fit, Sean Ellis test, growth hacking, referrals, first-time user experience, optimization
Timestamps: (00:00:00) Intro (00:1:55) The Origin of the Sean Ellis Test (00:13:13) Finding Product Market Fit Using the Test (00:18:21) Focus on "Must Have" Users (00:21:38) Growth Vs Marketing (00:25:38) Old School vs New School Marketing (00:30:17) 4 steps to growth (00:36:24) Improving Sign ups to Usage (00:41:37) The impact of Referrals (0045:31) One Piece of Advice
He sold AI robots to Walmart & raised $150M. His #1 advice to founders? "Trust your gut." | Daniel Theobald, Founder of Vecna Robotics
12 Aug 2024
00:38:04
Daniel's been building robots for 20 years. He's sold 100s of AI robots-as-a-service to Walmart, FedEx, & DHL amongst others. Last month, he raised a $40M round.
6 years ago, he realized why robots weren't getting massively adopted. Builders like him were trying to build perfect robots that always worked. But every situation has edge cases. What if you designed robots to work only 80% of the time and use humans for the other 20%?
That one unique insight changed everything and was the reason he started Vecna. His robots can tell when they need help and ask humans to assist in real-time.
Like most capital-intensive startups, Daniel played on hard-mode. Here's how he built hardware, robotics and AI, sold enterprise contracts, and grew to $10s of millions in revenue.
Takeaways
Why as a founder you need to trust your gut and stick to your convictions.
How to be objective and create an accurate model of the world to predict the future and make informed decisions.
How to bootstrap even a capital intensive company in robotics
(00:00:00) Intro (00:02:05) The Beginning of Early Robotics (00:06:00) Edge Cases in Robotics (00:08:15) Robots Shouldn't be Perfect and AI Isn't Intelligent (00:14:05) Technology Empowers Humans (00:18:19) When Robots Need Help (00:21:29) The First Pilot and Customers (00:29:49) Covid Slowed Everything (00:33:52) Finding Product Market Fit (00:34:45)One Piece of Advice
He spent 5 months working with customers before building—then grew to $10s of millions ARR. | Aviv Leibovici, co-founder of Buildots
22 Sep 2025
00:48:10
Aviv spent months walking construction sites carrying tools for managers just to understand their problems—speaking to customers is "bullsh*t"—you need to work beside them to see reality.
His company Buildots had a working AI product that tracked construction progress perfectly, but 90% of users got zero value from it. Until he made one key change that took them from barely surviving to 3-4X yearly growth.
He reveals why his first customers had negative margins, how he accidentally underpriced by 10X, and why you should never build a feature until you've proven the value manually in Excel first. After nearly dying, today Buildots does tens of millions in revenue.
Why You Should Listen:
Why you need to stop talking to customers and start working alongside them.
Why one simple change can transform usage and value creation.
Why you should prove value without product before writing a single line of code.
How to price when you have no idea.
Keywords: startup podcast, startup podcast for founders, Buildots, Aviv Leibovici, construction tech, customer development, product-market fit, B2B SaaS, computer vision,
00:00:00 Intro
00:01:41 From Israeli intelligence to construction tech
VCs give a lot of advice— & a lot of it sucks. Be careful who you listen to.
08 Aug 2024
00:07:32
Advice is free—actioning bad advice isn't. Early-stage founders are bombarded with advice. A lot of it from investors who have never operated a business, never ran marketing, never led sales.
And yet, many founders take VCs' advice as sacrosanct. And many VCs feel like they can and should opine on everything. If many people treat you like an expert, you must be one... right?
VCs have a lot to offer founders. But, like everyone, they have circles of competence.
Be careful who you listen to.
Why you should listen
Why power dynamics between VCs and founders can distort decision-making and advice-seeking.
Why you should be skeptical of advice that is outside of a VC's circle of competence.
Keywords customer needs, business problems, power dynamics, VCs, founders, advice
He took 3 years to make his 1st sale—then grew 1000x to $10M ARR 3 years later. | Alex Hoff, Founder of Auvik
05 Aug 2024
00:46:34
Alex got the co-founder of a public company to join him and raised $6M out of the gate—but it took him 3 years to make his first sale.
But after he shifted from selling to SMBs to selling to MSPs (Managed Service Providers i.e., outsourced IT), things took off:
April 2015 - $1K MRR August 2015 - $10K MRR June 2016 - $100K MRR Nov 2018 - $1M MRR ($12M ARR)
And growth never stopped—soon, he'll cross $100M ARR.
Alex and his co-founder did many things differently. They came up with an idea by starting with markets, not customer problems. They raised a lot of money upfront and built a sophisticated product instead of an MVP. And they deliberated cultural values before making their first hire.
Clearly—it worked.
Why you should listen
Learn why you should define culture before making your first hire.
How to find market trends and customer problems top-down instead of bottoms-up.
Why keeping your product unchanged but targeting a different market can have a massive impact and lead to product-market fit.
Why you should be willing to be bold and not hedge.
Why you should only focus on one thing at a time.
How to use constraints to do more things faster.
Keywords
Auvik, software company, networking, SMBs, mid-market, decoupling, control plane, hardware, software solution, automate, configuration, user research, product design, team, company values, SaaS, IT management, product-market fit, pivot, managed service provider, MSP, boldness, discipline, advice
Timestamps (00:00:00) Intro (00:01:47) The Origin of Auvik (00:07:20) Finding a co-founder (00:12:35) It's People Who Build Companies (00:14:10) Finding the Concept for Auvik (00:20:07) Buikding the Product (00:30:30) First Customer Experiences (00:34:40) Feedback Loops (00:39:08) Getting to a Million (00:41:33) Finding Product Market Fit (00:42:54) One Piece of Advice
If you wake up with your heart pounding out of your chest— do this.
01 Aug 2024
00:12:42
When an employee unexpectedly quits, an investor backs out, or a big customer churns— fear of failure takes over. When you close a new round, land a big customer, or make a big hire— you feel pure excitement.
Every founder is on a fear-excitement spectrum. There's no way to prevent yourself from feeling the two extremes. But I've seen great founders use several tactics to help themselves operate out of excitement more often than out of fear.
Those founders also feel fear— but they use these tactics to spend more time closer to excitement. Because operating out of failure is playing not to lose—whereas operating out of excitement is playing to win.
Here are 3 ways to do just that.
Why you should listen
How to use multiple plans to operate more freely and objectively
Why runway and low burn are the keys to lower founder stress
Why working with the right investors is more important than raising big rounds
What Tobi Lutke (founder of Shopify) did to change his employees' mindsets
Keywords founders, fear, fear of failure, excitement, validation, runway, partners, mindset, expectations
He refused to quit his job until $1M ARR—then grew to $5M ARR & closed a $25M Series A. | Pierce Ujjainwalla, Founder of Knak
29 Jul 2024
00:43:31
Pierce launched a consulting business that grew to millions in revenue and dozens of employees. But he noticed his customers kept asking for the same solution.
So he launched Knak, an email marketing and landing page builder that integrates to Marketo. Unlike most founders, he didn’t go all-in. He kept working on his consulting business full-time until Knak hit $1M in ARR.
After he transitioned over to Knak, he bootstrapped it to $5M ARR and then raised a $25M Series A. Here’s the story of how Knak found product-market fit.
Why you should listen
How to transition from a consulting/services business to a scalable tech startup-- and why it might be more painful than you think.
What you need to do to shift from SMB to midmarket and from midmarket to enterprise.
How to use enterprise customers to scale to $10M+ without needing thousands of customers
How to balance urgency and patience to build a successful startup
Time Stamps: (00:00:00) Intro (00:08:50) The Story of Knak (00:11:04) Going from Zero to a Million (00:16:16) Pivoting from SMB to midmarket (00:19:42) Adding "obvious" features to get closer to PMF (00:24:07) How to position against incumbents (00:27:35) Turning Into a Enterprise Platform (00:30:30) Finding True Product Market Fit (00:33:34) Bootstrapping to Series A (00:40:02) One Piece of Advice
99% of founders SUCK at storytelling. Here's the pro who taught Slack & Salesforce how to do it. | Matthew Dicks, professional storyteller & bestselling author of Storyworthy.
25 Jul 2024
01:17:39
There is no better storyteller in the world than Matthew Dicks. He tells stories for a living. He gets paid by the world's biggest brands to create stories for them. He's won Moth StorySLAM (a storytelling competition in NYC) a record 59 times.
Every founder knows storytelling is a critical skill. But 99% of founders I meet are terrible storytellers. They overcomplicate, they include too much information, they try to convince with data.
Like Matthew says, "Most of what people say in business is forgettable".
Whether you want to close customers, investors or employees, you need to stand out and be remembered. And the best way to do that is to tell compelling stories that resonate.
Here's how to do it.
Why you should listen
Why the key being remembered is being different
How to use stories to stand out and resonate with customers, investors and employees
Learn how to tell an effective story that is relatable, creates suspense, and includes personal connections.
How to use personal stories to sell more product.
Why you often shouldn't start a story at the beginning.
Keywords
storytelling, business, relatability, suspense, personal connection, Slack, Salesforce, communication, connection, simplicity, contrast, value proposition, trust
Timestamps (00:00:00) Intro (00:02:52) A Story About Why Storytelling is Important (00:11:18) Deconstructing the Story (00:15:07) Keeping a Story in Present Tense (00:16:58) Start With Location and Action (00:20:41) When to Tell a Story Chronologically (00:28:13) The Story for Slack (00:35:33) Making a Pitch with No Data (00:41:51) It's not B2B or B2C-- it's H2H (00:47:57) The Goal is to be Remembered (00:52:23) Use Truth in Your Story for Relatability (00:55:11) Making up stories on the fly for portfolio companies
In 2019, he went all-in on AI, grew to $3M ARR in 2 years—then to $85M ARR in 5. | Shubham Mishra, Founder of Pixis
22 Jul 2024
00:39:26
5 years ago, Shubham had just graduated college and had no network. He bootstrapped to $3M in ARR, then raised $200M & grew to $85M ARR.
But he started trying to sell AI for marketing to enterprises with no network.
So for 2 months, he'd go to the lobby of a bank and sit there for an hour. He'd wait for the CMO to walk by, just so he could say hi. He'd tell receptionists he was waiting for an interview.
Finally, one day the CMO had enough and asked him who he was. Shubham got his 15-minute moment. That turned into a free pilot.
That free pilot turned to $1.2M ARR.
2 years after he'd started the company, he bootstrapped to $3M ARR and was profitable— since then, the growth never stopped.
Why you should listen
How to start a startup top-down from a market vs bottoms-up from customer problems.
Why doing insane things in the early days can lead to insane results.
How Founder-led sales and tight feedback loops are the key for product development and customer success.
Keywords AI startup, product market fit, challenges, marketing, scaling, fundraising
Timestamps (00:00:00) Intro (00:01:52) Origin Story of Pixis (00:07:05) Getting the First Customers (00:09:14) What is Pixis (00:11:26) Video Generation (00:14:54) Finding the Problem Going Top-Down (00:19:55) The Pitch (00:24:30) The First Pilot (00:27:08) Scaling the Team (00:31:57) Raising the First Round (00:33:59) The AI Market (00:35:54) Finding True PMF (00:37:13) One Piece of Advice
How Wiz grew to $500M ARR in 4 years—& could exit to Google for $23B (largest VC-backed exit in history)
18 Jul 2024
00:11:11
Google is in talks to buy cybersecurity startup Wiz for $23B (a 40x revenue multiple). Wiz is the company that in 2021 announced it grew from $0 to $100M ARR in just 18 months.
How did this cybersecurity company grow so fast in a crowded space?
How does it get a 40x revenue multiple when FAANG stocks trade at 5-15x?
Who are the exceptional founders that were able to create the largest venture-backed exit in history in just 4 years?
In this episode, we dive into the 3 ingredients that made Wiz into such a success: insane growth, insane team, and insane discipline.
Why you should listen
Why addressing a full 'Job to be Done' is key to fast growth
Why having an A+ team is irreplaceable
Why you need several factors to come together to have exceptional, outlier results
Timestamps: (00:00:00) Intro (00:01:00) Wiz's 3 Ingredients to Success (00:01:09) 1. Insane Growth (00:02:30) Jobs to be Done Framework (00:03:30) What does Wiz do? (00:05:36) 2. Insane Team (00:07:54) 3. Insane Discipline
He built a farming robot that shoots weeds with lasers— then closed $10M in pre-sales before shipping a single one. | Paul Mikesell, Founder of Carbon Robotics.
15 Jul 2024
00:58:20
Paul built a startup that was acquired for $2.2B. He worked on AI at Uber and Oculus. But when a farmer told him about some of the problems he was facing, he quit and went all-in on farming.
He built a robot that attaches to the back of tractors, uses computer vision to identify weeds and lasers to shoot and kill them. He sells each robot for $1.5M. He's sold nearly 100 so far— & generated nearly $150M in revenue.
Whether you're working on a hardware startup or not, you'll want to listen to this episode to see how to do proper customer discovery, how to raise pre-product, and how to get millions of dollars in pre-sales without having to ship.
Why you should listen
Why hardware is hard-- but easier than it's ever been.
How to tell a story to raise $10M pre-revenue
How to set up milestones for fundraising
How to generate $10M in pre-orders before shipping product
How to get a sense of product market fit even before the product is fully developed
Keywords
Carbon Robotics, deep tech, AI neural nets, deep learning, weed control, farming, manual labor, lasers, research and development, funding, seed round, prototype, Series A, pre-orders, manufacturing challenges, revenue
Timestamps: (00:00:00) Intro (00:02:09) A Background in Deep Tech (00:05:50) Problem and Solution Interest (00:07:35) Find the Passion (00:07:37) Get Behind the Mission (00:09:39) Back to Seattle (00:11:40) The Epiphany (00:16:50) A Human Affair (00:18:00) The Money Flows to the Best Storyteller (00:21:45) A Farmer's Weed Control Dilemma (00:25:56) Weed-Shooting Lasers (00:28:11) Funding the Prototype (00:30:13) Hardware is Hard But Rewarding (00:36:46) Why Laser Weeding Works (00:41:19) Series A (00:42:51) Robot Autonomy (00:45:42) Pricing (00:48:12) Telling the Story After It Happened (00:51:44) Fighting Through Disaster (00:54:50) Finding True PMF (00:55:41) One Piece of Advice
Tesla’s EV market share (finally) falls below 50%. Good news for founders— incumbents took 15 years to match 1 founder.
11 Jul 2024
00:06:58
Elon Musk single-handedly took on the entire automotive industry. No one, including me, thought he would succeed. But he's built an $800B company. Whether sales are slowing down misses the mark: the punchline is it took well capitalized, professional automakers 15 years to catch up to a single founder.
Sure, Elon Musk is special. But this goes beyond just Elon Musk. It shows that founders today have more business power than founders have ever had. They can take on the most established industries.
The reason is that the pace of innovation is faster than ever. No business model is safe.
And founders are the only ones who can react.
Keywords Tesla, EV market, car manufacturers, Elon Musk, disruptive innovation, business models, founders, rate of change
YC founder raises $3.5M, keeps team to 3 people—then grows 10x to $2M ARR in 1 year. | Benjamin Encz, Founder of Ashby
08 Jul 2024
00:34:46
Last month, Ashby raised a $30M Series C. Ashby is used by customers like Notion, Ramp and Sequoia. Benji built Ashby as an end-to-end Applicant Tracking System (ATS) that would replace several point solutions. He had to build heads down for 18 months and couldn't launch a simple MVP.
Surprisingly, even though he raised $3.5M at seed, he didn't grow his team. He built the product with just 3 people. "We could spend time recruiting or we could spend time building"-- he decided to build.
When they launched, they grew to $200K in ARR within a year and then 10x'd a year after that. Here's the story of how they found product-market fit.
Why you should listen
Why keeping your team small helps you go faster.
How to displace point solutions with an end-to-end platform
How to validate pain points.
How to move up market from startups to enterprise companies.
Keywords Ashby, all-in-one platform, recruiting, reporting, pain points, product market fit, Series A
Timestamps: (00:00:00) Intro (00:01:29) No Website, No Problem (00:03:08) A Viral Loop (00:04:40) Origin Story of Ashby (00:05:39) The Biggest Pain Point (00:07:50) De-Risking (00:09:26) A Sticky Product and Market Evolution (00:10:50) A Hundred Conversations (00:13:09) The Main Feedback and Key Learnings (00:16:16) The Pitch (00:17:20) Bundling and Unbundling (00:20:50) Building a Great Engineering Organization (00:22:26) Letter of Intent Stage (00:24:45) Validation and Feeling Ready (00:28:18) A Little Bit of Luck (00:31:51) Finding True PMF (00:32:44) One Piece of Advice
She cold messaged 50,000 engineers—then grew to $10M+ ARR. | Shensi Ding, Founder of Merge
18 Sep 2025
00:40:16
Shensi cold messaged 50,000 engineers to build Merge. She worked 9am-9pm every day, gave her first customers two months free to prove herself, and refused to hire anyone remote—even during peak COVID.
She purposefully didn't collect a single dollar of revenue until she knew she could hit $1M in a months. "Startups are all about momentum."
She lost their biggest deal to a competitor who copied them, then won that customer back years later. She outbounded her way from zero to $10M through sheer force of will, doing demos all day until her calendar was completely booked. Today Merge has raised $75M and powers integrations for hundreds of B2B companies.
This is raw, unfiltered founder advice from someone who believes you just have to "man up" and outbound your way to success.
Why You Should Listen:
Why you should wait to collect revenue until you see a clear path to $1M ARR.
Why you need to outbound thousands of people to build your team.
You can will your way to $10M—but you'll need something else to hit $100M.
Why they are an in-office company, even for remote rockstar devs.
Pickleball grew 3x in 4 years to 14M players. Not by competing with tennis— but by creating a new market instead.
04 Jul 2024
00:09:01
AI startups don’t necessarily have to beat incumbents. Some will start entirely new markets instead.
Like Canva to Photoshop, Shopify to Amazon or Pickleball to Tennis, many of these won’t even have to compete. They create 10x easier to use products and through that open up an entirely new space. They solve problems people didn’t even know they had. In many cases they expand the market for incumbents too— pickleball didn’t steal tennis players, it became a gateway and created even more.
We discuss the 3 factors a startup needs to be able to create a new market and why there is plenty of opportunity left in the AI space.
He fought Al Qaeda in Iraq, turned down $250K at McKinsey—& built a $150M+ ARR unicorn. Here’s how it happened: | Blake Hall, Founder of ID.me
01 Jul 2024
00:52:41
"I was technically homeless at the time. I was sleeping on my buddy's couch. I had declined $250,000/ year at McKinsey... I had no idea what I was doing." Now, Blake has $150M in ARR, growing 30% per year, with 80% gross margins. He's raised $400M and his startup ID.me is worth over $1B.
This is the story of how pivoted for a Groupon-like model to an identity verification platform. Blake talks about how he raised the initial round, closed the first few enterprise contracts, and why he thinks finding product-market fit is more of a science than most founders think.
After his pivot, ID.me doubled its user base every year. Now, over 40% of Americans have an ID.me account.
Why you should listen •Learn how even successful founders are often much closer to failure than you'd expect •How to get credibility as a founder and close enterprise deals. •Why fear of failure can be a powerful motivator if used constructively. •How to use a niche market to quickly find product-market fit •Why staying close to customers is the best way to pivot into the right problem/solution set.
Keywords ID.me, military, tech founder, product-market fit, startup, business model, capital raising, mentorship, scientific approach, user base, revenue growth
Timestamps: (00:00:00) Intro (00:01:56) The Origin of ID.me (00:04:44) The Two Parts of Credibility (00:11:16) To Win Big, Start Small (00:14:53) Fear of Failure Can Be Positive (00:20:54) Paypal for Identity (00:23:59) Moving to DC and Raising 500k (00:27:53) Belief in the Person Over the Business Model (00:30:55) Pivoting to Identity Wallets (00:41:07) The first big contract: Under Armour (00:48:06) Getting to a Million (00:49:39) One Piece of Advice
Each Google/OpenAI update kills more startups. Here’s how to make sure you're not next.
27 Jun 2024
00:10:33
Every startup needs to compete with incumbents. But it's different with AI.
AI startups need to create websites or apps from scratch and drive traffic. Incumbents can just add AI as a feature. They have distribution built in.
AI is not like previous tech revolutions. Unlike mobile, the internet, or the PC revolution, AI is not a new distribution channel. Startups are at a much bigger disadvantage than they've ever been.
In this episode, we discuss the 3 key elements you need to consider to answer the most important question:
Will you get distribution faster than incumbents get product?
Keywords AI, startups, incumbents, distribution channels, technological shift, mobile, internet, PCs, sustaining innovation, disruptive innovation, product versus distribution, founders
Why you should listen
This time it's different. AI is easier for incumbents and harder for startups than previous tech revolutions.
Startups need to consider the incumbents they are up against, the power dynamics in the market, and the primary use case they are targeting.
Understand how to think through the race and what elements are most important