SaaS Interviews with CEOs, Startups, Founders

How I Turned my Podcast into a $50m ARR B2B SaaS

We just hit $400m in revenues. Here are 9 org chart, people moves I had to make to scale

Jason Cohen founded WPEngine in 2010 and broke $20m within 4 years. Today, the company does $400m+ in Revenues. In this podcast Cohen teaches 9 rules he used to change his org chart, optimize roles, and replace himself as CEO as he scaled. Will they break $500m revenue this year?

27 year old Founder exited for $169m at $50m ARR. How much cash did he take home at exit?

Ryan Allis launched iContact when he was 18. He made $15m cash when he exited in 2011 for $169m. He shares his negotiation with Salesforce Marc Benioff, how he found 10 profitable acquisition channels, 70,000 customers, and broke $50m in revenues. Will he buy it back for $1 one day?

This Danish CEO Hit $30m ARR using Unique 14 Hub Model Selling Software for Microsoft Ecosystem

LMS365 raised $20m in 2023 at a $100m valuation - a 5x multiple on $20m of ARR. As of April 2024, they do $30m in ARR. Their 200 person team is focused on building software for the Microsoft ecosystem. Can they hit $40m ARR this year?

How Younium Hit 200 Customers Paying $30k ACV For its Billing and Revenue Analytics tool

Genius SaaS Pricing Page Generated $3m in Revenue Last Year

They hit $3m ARR fast using MTU tiers on their pricing page. Raised $7m in 2023 at a $35m post money valuation and are burning $30k per month today. Focus is profitability before Q2 2025, will they hit it?

39 Year Old Made $21m Last Year Selling Surprising Software

Rural mom and pop shops love him. 13,000 have purchased his POS and software system processing over $1.85 billion in GMV in 2023 across 35m transactions. Can he crack $2b GMV in 2024?

How Bootstrapper Made $6m Last year Using New Self-Funding Method

Companies like Samsung are sourcing college talent using Scholarship Owl. The firm hit $6m in 2023 revenue, bootstrapped. 150,000 college students join the platform monthly increasing the size and quality of the talent pool the company’s B2B customers can pay to access. Can he hit $10m this year?

How to turn your sales playbook into a revenue machine that adds $Xm in new ARR per quarter

Miami Based Fintech did $70m in 2023 Revenue - What about Gross Margin?

CEO Alex Shvarts shared a default rate of 15%, charge off rate of 6.8%, along with significant expenses related to acquisition costs, and interest expenses. The firm is targeting $300m in capital deployed in 2024. If it hits its target, does this FinTech SMB factoring company have enough margin to survive long term?

This Software for Doctors hit $51m revenue last year (100% growth). $5m profit.

Reveeler grew ARR 100% from $25m to $51m in 2023 and took $5m to the bottom line as profits. What interest rate do they pay Hercules on their new $65m debt facility for acquisitions? How does CEO Jay Ackerman plan to hit $100m in revenue this year (2024)? Who will they acquire next?

Do these 9 things to ensure your way to $50 Million ARR

20 year old wins $3m playing Poker, launches $4m bootstrapped SaaS

20 year old wins $3m playing poker, launches SaaS. He raised $18.2m. After 7 years and dilution down to under 50% he left to launch his new bootstrapped company. Whippy helps lawyers run their operations and hit $4m ARR this month. Can he hit $10m bootstrapped?

51 year old dad raises $31.5m to help companies do meter based billing

CEO Griff Parry launched m3ter in 2020 after selling his first company Gamesparks to AWS. Today 10-100 customers pay him platform fee's and usage fee's to use his usage based billing API tool. He doesn't code but across his team of 56, more than 25 are engineers. Can they scale into their last round valuation?

He Did $1m last year selling South American Business Data to firms like CapIQ

Solo Founder, No Employees, Exits for $1m+ Keeps 100%

Launched in 2016 selling software to Music Repair Shops, TudoDesk exited for $1m+. This is the low stress, high wealth way to build a software company. TC won't write about you, but it doesn't matter, you'll get wealthy fast!

This CEO Does $20m/year Selling Software to Chiropractic Offices

Launched in 2016, CEO Matt Prados got rich off dividends and profits. He's bootstrapped to $20m in revenue with plans to hit $32m in 2024. Can he do it? His outbound call center strategy might get him there. 

How he's going to ask 30 beta users to pay $1k/mo for his Partner Management Software

This Mom of 2 Wants to help Hotels Clean Sheets Faster but needs to update her Andriod App first

She's using her marketplace to fund $1m in ground heating systems in Finland and charging a SaaS Fee

Tarja recognizes that energy in Finland is a hot space. She's launched a marketplace connecting 100 apartment complex owners with 100 providers of energy services like solar and heat. Shes raising a $15m fund to then back these projects that go through her marketplace. Will she get the $15m SPV closed and change the course of energy efficiency before 2025?

How this 1 person team did $2m in Revenue Last Year

Suzy.com did $65m Revenue Last Year. 18% was services so how did he keep 75% gross margin?

Matt Britton sold his agency for $50m in 2010 then launched Suzy.com in 2011. The original version, Crowdtap, was a mobile app where consumers could test new enterprise products like candy bars, detergents, and other items. The firm struggled and then doubled down on Enterprises paying for user research through its software, hitting $10m Revenue in 2018. Last year the firm did $65m in revenue and burned $12m. Britton says “We’ll hit $82m revenue this year and plan to burn $9m with a track to...

Proof you can build a $2m SaaS in any Niche (even with big competitors!)

Despite large competitors like CloudBooking, Guesty, and other hotel management platforms, RoomChecking CEO Jonathan Weizman has carved out a $2m niche. He specifically helps hotel owners in France organize cleaning schedules by hotel cleaners as guests check out. 

How to Make $3m Building a Slack Clone with no money, experience, or sales team

He turned down $20m in 2021 for his Slack competitor, Chanty.com. Today, the company has over 24,000 paying customers and does $3m revenue, profiting $1.2m in 2023. The company is fully bootstrapped. Can he find a sales co-founder willing to hustle hard for 15% equity?

Why he shut down his $40m Revenue Grocery company and moved into data recovery

He raised $16.9m and hit $40m in revenue. Success? Wrong. He shut his unprofitable grocery delivery company down in 2021 then spent a year working with liquidators. Today, he’s moved industries to the Dev Ops space and launched his disaster recovery SaaS Bennudata.com. 

How To Make $30,000 Instantly off a Viral Linkedin Post

His first company grew to a few million in revenue before exiting in 2021. After a 2 year earn-out, he left to build a new company. When his Customer Health Tracking excel template went viral on linkedin, he capitalized and launched his SaaS. The post led to 6 customers paying $500/mo for his revenue operations platform, Revos.ai 

How to Double Your Company From $16m to $30m Revenue Using Multiple Product Lines with Chilipiper CEO

After Tiger gave the founders $7m in a 2021 secondary at a $625m valuation, they took their team to Morocco for a team retreat. Seeing a weak market, they chose to cut the team from 225 down to 150 and become profitable. Despite these cuts, they’ve doubled revenue by selling 5 key product lines to sales teams. Will they do $50m in revenue in 2024? Chilipiper.com

How to Generate $6m of Revenue and keep 100% Equity with BadgerMaps CEO

His 13 person sales team does 2,000 calls per month. This engine has landed him 4,100 customers who pay him to help plan their field sales reps driving routes to save gas and make more money. He’s bootstrapped the company to $6m and made a full recovery from COVID down year 2021. He’s used debt to scale to keep 100% equity. Will he get the exit he dreams of in 2024 and reap the rewards of bootstrapping and keeping equity? Badgermapping.com

Fireside Chat with James Isilay of Cognism: Fundraising during the current economic climate

How to build a $4.5m revenue company with 0 Full Time Employees

300,000 homeowners cut their lawns every month with Greenpal who connects them to 35,000 lawn care companies. In 2023, the company did $30m in total lawn cuts and kept 15% of that revenue to generate $4.5m in revenue. They do this all with 0 FTE’s. Why? Bryan wanted freedom. He wanted to travel 11 months of the year while building a company he loved. VC wasn’t an option. Listen in if you’re looking to build a business and life you love with no external pressure. Yourgreenpal.com

Masters of Debt: How I bought a $5m SaaS Company Using Debt, Grew to $20m, Then Flipped for a Huge Gain

How PandaDoc Uses CI to Manage 800 Product Updates Per Month on Path To $100m+ ARR

How I raised a $15m Series B in a downturn

$100m in revenue selling software to 27,000 AirBNB hosts?

Smart way to use ZoomInfo to get first $60,000 in B2B SaaS Sales

How to build a $30m SaaS in 18 Months focusing on an unsexy niche

How to land your first $5k SaaS Pilot

How to raise $500,000 with no code, no customers, and not based in the US

Founder Hits $13m Revenue with No VC Raised selling SaaS to Defense Firms

How This Founder Plans to use AI to help Remote Sales Team Managers Run Better Teams

This founder has spent 12+ months in R&D with no revenue. He generates income from consulting. Will his SaaS ever take off if he keeps his consulting job as a safety net?

How to do $500,000 Revenue in 8 Weeks launching new AI SaaS Tool

AI is a buzz word. No one asks "Can I buy AI". Ideally, they want your product, which happens to be better than everyone else because you use AI. This CEO is taking advantage. Can he hit $1m in ARR in his first 16 weeks?

Bootstrapper Reveals $7m Profits on $40m Revenue Selling to Banks, 2 Customers Pay $10m+ Each

Launched in 2012, this company hit $1m revenue 1 year after launch. Today, they do $40m and the founder still owns 69%. 17% investors. 14% ESOP pool. Can he bootstrap to $100m by 2026?

First time Kenyan Founder Uses $1.50 FB Ads to Get First 100 Users, 64 DAU

SaaS is worldwide. This Kenyan based founder creatively used underpriced FB ads to get new users for $1.50 each. 60% of signups are still active on a daily basis. Will they convert to paid when he launches his paywall?

18 Month Old Startup Already Has 3 Customers Paying $100k/yr. Is AI over valued?

Most founders think you can't launch and ask customers to pay $100,000 per year. This founder got his first 3 customers to pay $100k each. He's managed to hold on to 80% of his company. How'd he do it?

He Hit $8m in Revenue Helping UK Companies Train Employees Faster and Comply with Regulation

Sometimes, government regulation forces companies to pay for software. Aptem has taken advantage of UK vocational law to hit 170 customers paying $40,000 per year on average. Can they break $10m revenue by December?

How he plans to convert to beta users into paying customers for his team collaboration tool

$50,000 is a lot of money for this founder. He's all in but still pre revenue. Whats holding him back from asking happy beta users to start paying?

He hit $120m in ARR Then Sold $70m Unit for $250m, Today His Secrurity SaaS is Cash Rich... whats next?

This security SaaS hit $120,000,000 revenue in 2022. Then they decided to sell a $70m business unit for $250m cash. Today they are cash rich with $50m in ARR. Who will the CEO acquire with all that cash? How fast will it take to get back to $100m in ARR?

How to Grow Faster with $0 CAC

How to launch a Newsletter, get 7k Subs, first $5k Sponsor. SaaS Next?

How Chaser hit $294K revenue and 3 person team in 2023