SaaS Club
PodcastPlaybooksCoachingSponsorFree ToolsJoin Community
saasclub

Helping SaaS founders build and scale profitable businesses since 2014. Powered by real experience from 475+ founder conversations.

Content

  • The SaaS Podcast
  • Founder Playbooks
  • Blog
  • Newsletter
  • Free Tools

Programs

  • Plus
  • Launch
  • Mastermind
  • Accelerate

Company

  • Contact
  • Become a Sponsor
  • Suggest a Guest
  • Terms
  • Privacy

© 2026 SaaS Club. All rights reserved.

Built with ❤️ for SaaS founders

Fundraising

Fundraising for SaaS Startups

How SaaS founders raised capital and what they learned. Seed rounds, VC relationships, alternative funding, and why some founders chose not to raise at all.

Real founder strategies. Delivered weekly.

Free weekly newsletter · No spam

Pendo raised $479M over multiple rounds and built a category-defining product analytics company. Proof raised $260M by riding the timing wave of remote notarization. Fyxer closed a Series B in just nine days based on their AI performance data. And Todd Dickerson never raised a dollar and grew ClickFunnels to $140M ARR. These episodes cover the full spectrum of fundraising decisions — including the decision not to raise at all.

You'll hear the unfiltered version of what fundraising is actually like. Drata raised early and reached $100M ARR before their fourth birthday. Assembled raised $71M from NEA, Emergence, and Stripe. But Gilles Bertaux at Livestorm raised a seed round and had no meaningful revenue for two years afterward. Kaveh Rostampor bootstrapped Planhat for six years before eventually raising, saying the discipline of bootstrapping forced them to create real value.

The practical advice covers the full journey: how to build relationships with investors before you need money, how to structure your pitch and data room, and how to evaluate term sheets. Egnyte's founder started with $100 in his pocket and eventually raised $137.5M to reach $300M-plus in revenue — proof that the timing and terms of your raise matter more than whether you raise.

There are also conversations about alternatives: revenue-based financing, bootstrapping with early revenue, pre-selling annual contracts, and creative approaches that don't involve traditional VCs. Whether you're preparing for your first raise or deciding if you should raise at all, these episodes will help you make a better decision.

Podcast Episodes

Browse by topic:AllBootstrappingFirst CustomersProduct-Market FitEnterprise SalesProduct-Led GrowthPricing & MonetizationFounder-Led SalesPositioning & DifferentiationChurn & RetentionContent & Inbound MarketingExits & AcquisitionsFundraisingAI-Powered SaaS
7 Years of Zero Revenue Then Product-Market Fit Hit - Rob Woollen

Rob Woollen, Sigma Computing

7 Years of Zero Revenue Then Product-Market Fit Hit

Rob Woollen is the Co-Founder and CTO of Sigma Computing, whose seven-year search for product-market fit led to building a data analytics platform that lets business users analyze cloud-scale data without writing SQL. Rob Woollen's journey of finding product-market fit is one of the longest in SaaS history. He founded Sigma Computing 11 years ago with a clear problem to solve: business users were stuck with spreadsheets while programmers got powerful cloud data tools. The first seven years were brutal. Rob and his co-founder raised $8M, hired a team of five, and built multiple prototypes - each one a "colossal failure." At one point, two founding engineers quit because they felt the company was "just swirling around." The team shrunk to three people for a year and a half. The breakthrough came in 2017 when their investors suggested meeting with Snowflake. In just 30 days before the meeting, Rob's team rebuilt their entire product to integrate with Snowflake's cloud data warehouse. At lunch, Snowflake's CEO said something they'd never heard before: "I want this. When can I start using this?" This was the first real sign of finding product-market fit after years of "polite feedback." But even after finding early traction and reaching $1M ARR, Rob made a controversial decision - rebuild the product again. He felt the interface still wasn't right, even though the company was finally making money. Today, Sigma Computing has crossed $100M in revenue with 600+ employees and 1,400+ customers.

From $5K Deal to Unicorn - A SaaS Fundraising Story - Jenn Knight

Frequently Asked Questions

Should I raise funding for my SaaS startup?+

Kaveh Rostampor bootstrapped Planhat for six years before eventually raising, saying the discipline of bootstrapping forced them to create real value. Gilles Bertaux at Livestorm raised a seed round and had no meaningful revenue for two years afterward. Egnyte's founder started with $100 in his pocket and eventually raised $137.5M to reach $300M-plus in revenue. Todd Dickerson never raised a dollar and grew ClickFunnels to $140M ARR. The choice depends on whether you need capital for a time-sensitive opportunity or can grow profitably from revenue.

How much traction do I need to raise a seed round?+

It varies wildly. Livestorm raised a seed round with essentially no revenue and spent two years finding product-market fit. Drata raised early and grew to $100M ARR before their fourth birthday. Assembled raised $71M from NEA, Emergence, and Stripe with a strong team and clear enterprise traction. Fyxer closed a Series B in just nine days based on their AI performance data. The bar depends on the market and investors, but having paying customers, strong retention signals, and a clear path to scale dramatically strengthens your position. Most seed investors want to see at least $5K to $20K in MRR.

What do VCs look for in a SaaS startup?+

Pendo raised $479M over multiple rounds. Their metrics told a clear story: strong product usage data, rapid enterprise adoption, and expanding revenue per account. Proof (formerly Notarize) raised $260M by showing massive market timing with remote notarization. Drata reached $100M ARR before their fourth birthday, proving execution speed. Fyxer's data showing AI outperforming humans closed their Series B in nine days. VCs evaluate market size, team execution ability, product-market fit evidence, and the potential for rapid compounding growth. Retention metrics and a founding team with unique insight into the problem matter most.

What are alternatives to VC funding for SaaS?+

Egnyte's founder started with $100 in his pocket and built to revenue before raising. Kaveh Rostampor bootstrapped Planhat for six years using customer revenue. Todd Dickerson self-funded ClickFunnels entirely from savings and early revenue. Stuart Crane started with $200 each and built to a $43M exit without outside money. Alternatives include revenue-based financing, angel investors, SaaS-specific lenders, pre-selling annual contracts, and government grants. Each has different trade-offs in dilution, repayment, and control, but the founders who bootstrapped consistently say it forced better discipline.

Get weekly SaaS insights

Real founder strategies. Delivered to your inbox.

Free weekly newsletter · No spam

←All Episodes

Jenn Knight, AgentSync

From $5K Deal to Unicorn - A SaaS Fundraising Story

Jenn Knight is the co-founder and CTO of AgentSync, a company modernizing how insurance companies handle agent licensing, compliance, and onboarding. In 2018, Jenn was working at Dropbox while her co-founder (and now husband) Niji was at Zenefits. He saw firsthand how insurance companies were struggling to keep their agents licensed and compliant. No one had figured out a good solution. Niji became so convinced there was an opportunity that he quit his job to work on the idea from their kitchen, while Jenn kept her day job at Dropbox and built the product evenings and weekends. As tech outsiders trying to break into the insurance industry, they got a lot of pushback. People kept telling them this wasn't even a real problem. After months of building the product and talking to potential customers, they finally landed their first customer who paid $5,000 a year for their solution. But everything changed after a product demo when insurance professionals started listing all the ways AgentSync could make their lives easier. Their excitement showed the co-founders they were onto something big. In late 2019, the couple took a huge leap of faith. When they found out Jenn was pregnant, she quit her job at Dropbox. They decided to move to Denver, where they'd both work on AgentSync full-time without any funding lined up. The timing seemed terrible. The pandemic hit just months later, but instead of failing, they thrived. Their SaaS fundraising journey took off - they raised their seed round, then their Series A, and grew to 35 employees by the end of 2020, then to over 100 the following year. Today, AgentSync has achieved unicorn status through successful SaaS fundraising rounds, pulls in eight-figure revenue, has over 250 customers, and employs more than 200 people.

How Firing 40% of Customers Ended a SaaS Churn Cycle - Caleb Avery

Caleb Avery, Tilled

How Firing 40% of Customers Ended a SaaS Churn Cycle

Caleb Avery is the founder and CEO of Tilled, a PayFac-as-a-Service platform that helps B2B software vendors embed and manage payment processing for their customers. In 2019, after four years of angel investing and consulting for vertical software platforms, Caleb spotted a pattern: companies processing $10 million a month on Stripe were leaving $800,000 a year in payment revenue on the table. The problem was not awareness - it was that switching off Stripe took six months of engineering time. Caleb spent 10 months as a solo founder validating whether he could compress that to one week. Once he convinced himself the idea was viable, he brought on a CTO and started building. The first version of the product was, in his words, "truly terrible." It took a full 18-month rebuild focused on white-label support and developer documentation to create something that could compete with Stripe. When COVID hit, Caleb's outbound sales and trade show strategy collapsed. With less than 500 LinkedIn followers, he pivoted to content marketing - hiring a ghostwriter for $800 a month and building a content library seven months before the product even launched. That bet on SaaS churn prevention through inbound paid off: LinkedIn drove 95% of Tilled's lead flow in the first year, getting them close to $1 million in ARR. But the rapid growth masked a SaaS churn problem. Of Tilled's first 50 customers, only 15-20 were finding real success on the platform. The rest consumed resources without scaling. Caleb made a gutsy call: he fired roughly 40% of his customers and narrowed the ICP to focus only on customers that matched the profile of those who were thriving. The result was 60-90 days of uncertainty followed by 25% month-over-month growth and eventually 500% year-over-year growth. A single podcast appearance also brought 36 channel partners inbound in 24 hours, opening a reseller channel that still drives deals today. Today, Tilled generates strong 7-figure revenue approaching 8 figures, serves around 100 customers, and has raised $40 million in capital.

5 Years to Build an Enterprise SaaS Nobody Thought Was Possible - Thomas Cottereau

Thomas Cottereau, SightCall

5 Years to Build an Enterprise SaaS Nobody Thought Was Possible

Thomas Cottereau is the co-founder and CEO of SightCall, a cloud-based platform that helps enterprises provide remote visual support for complex customer issues. In 2008, Thomas was working as a telecom engineer when he and his friend had an idea. They wanted to create a solution that could bridge the gap between the world of telecommunications and the internet. So, they started working on what would eventually become SightCall, spending their evenings in his friend's basement to bring their vision to life. They bootstrapped the company for 3 years, creating a prototype in just 4 months. However, building a scalable, enterprise-ready platform took 5 challenging years. In 2012, Thomas started showing up at Salesforce's San Francisco office every week, determined to get a meeting. Despite facing repeated rejections, he persisted until he finally secured the meeting he was after. Their prototype and unique approach impressed Salesforce, leading to a pivotal partnership that helped them land HP as their first major customer. Using SightCall, HP could remotely guide customers through printer issues, fixing problems without dispatching technicians or handling returns, saving millions in product returns. But getting to this point was no easy feat. It took years of hard work, constantly improving the product, and never giving up. And even after landing HP, it was just the beginning of the challenges they would face. As SightCall grew, they encountered numerous obstacles. Legal issues forced them to rebrand, sales and marketing teams clashed, and the pressure to scale rapidly intensified after raising significant funding. Today, SightCall is an 8-figure ARR business serving hundreds of global enterprise customers with a 100-person team. They've raised $54M to date.

From Google PM to SDR - Founder-Led Sales at DoControl - Adam Gavish

Adam Gavish, DoControl

From Google PM to SDR - Founder-Led Sales at DoControl

Adam Gavish is the former co-founder and CEO of DoControl, a SaaS security solution that helps companies protect sensitive data stored in their SaaS applications. In 2020, while working as a product manager at Google, Adam faced the challenge of securely sharing sensitive company data with external partners. The experience made him realize the need for a better way to balance security and productivity. Adam eventually teamed up with a friend to validate their idea. They leveraged their network to connect with 50 security professionals, spending three months interviewing them and digging into their challenges. After building confidence in their idea, the founders traveled to Israel for a week and pitched to 22 VCs. All but one rejected them, but thanks to that one VC, the founders raised a $3 million seed round. With funding secured, the founders formed a small team and collaborated with early design partners to develop an MVP. They also went back to the security professionals they'd interviewed in the hope of landing their first customer. After three months, they reached a point where one company saw enough value to pay $2,000 annually and become DoControl's first paying customer. To grow further, Adam had to take on the role of SDR, even though he had no prior sales experience. He found himself sending hundreds of LinkedIn messages each week, hoping to book customer calls. Despite the challenge of learning sales from scratch, Adam persevered and slowly started to gain traction with customers. But as the company grew, the crowded cybersecurity market made it increasingly difficult for DoControl to communicate its unique value proposition. This became an uphill battle for the founders. However, despite those challenges, the founders have grown DoControl into a multiple 7-figure ARR SaaS company and raised $43M in funding.

SaaS Fundraising After Being Told She'd Never Raise - Stephany Lapierre

Stephany Lapierre, TealBook

SaaS Fundraising After Being Told She'd Never Raise

Stephany Lapierre is the founder and CEO of TealBook, a supplier data platform that helps enterprise customers make better procurement decisions. In 2014, Stephany launched TealBook, initially as a service where she sold $5,000 memberships to suppliers selling to enterprise customers. However, she realized this model couldn't scale when a larger customer wanted data on hundreds of thousands of suppliers, rather than just a few hundred. After years of bootstrapping TealBook from her living room while juggling the responsibilities of raising three children, Stephany faced a pivotal moment. She realized she needed to transform TealBook into a software platform. But SaaS fundraising was really tough for Stephany, mainly because investors were skeptical about her being a solo founder without a tech background. One investor bluntly told her, "You'll never raise capital on your own. You've got three kids, a funny accent (she's French Canadian), and you've never built a tech company." Despite these challenges and harsh feedback, Stephany rose to the occasion. She knew she needed a strong team to get investors on board, so she found a CTO who shared her vision for TealBook and together they got to work. By 2017, she successfully raised the funds they needed to grow the company. Today, TealBook is a 7-figure SaaS business, with over 100 enterprise customers. The company has raised $72M in SaaS fundraising and grown to a team of 60 people.

From Race Car Driver to Vertical SaaS CEO at 60 Airports - George Richardson

George Richardson, AeroCloud

From Race Car Driver to Vertical SaaS CEO at 60 Airports

George Richardson is the co-founder and CEO of AeroCloud, an airport management platform that helps airports optimize operations and revenue using AI and machine learning. In 2017, after retiring as a professional race car driver, George was looking for a new challenge. He randomly met Ian at a coffee shop in England. Ian had previously built and sold an on-prem software product for airports. Together, they decided to build an app to help airlines resell last-minute plane tickets. But they struggled for two years to gain traction. The airline market was brutal - thin margins, demanding buyers, and no clear path to a category-defining company. Eventually, they asked themselves a simple question: why not take Ian's proven on-prem airport management software and reinvent it for the cloud? They pivoted and started building a vertical SaaS product for airports. But even with Ian's domain expertise, signing those critical first customers proved difficult. Nobody wanted to be the first airport to adopt mission-critical software from an unproven startup. A breakthrough came at the Florida Airports Council conference. After emailing every attendee and getting zero responses, George spent three days floor-walking and getting rejected. Then at 4pm on the last day, a text came from a guy named Parker: "I'm at the bar. You can buy me a beer." By 11pm, they had a handshake deal. If AeroCloud built specific features for his airport, Parker would pay. Within three months, Ian built the product. Parker became their first customer, then evangelized AeroCloud to other airports. Tampa International signed on as their second customer - and actually paid AeroCloud to further develop the product. That revenue, combined with venture capital, launched their vertical SaaS growth engine. AeroCloud scaled from $200K ARR without outside funding to raising nearly $18 million across seed and Series A rounds. They nearly ran out of runway before their second raise when lumpy enterprise deals missed their timelines. But their seed investors led the follow-on round, and a quarter later revenue tripled. Today AeroCloud serves 60 enterprise airport customers, employs 60 people across the US and UK, and generates multiple millions in ARR.

How Picking One Customer Type Drove 8-Figure ARR - Itai Sadan

Itai Sadan, Duda

How Picking One Customer Type Drove 8-Figure ARR

Itai Sadan is the co-founder and CEO of Duda, a professional website builder for digital agencies and SaaS companies. In 2009, Itai and Amir, both at SAP, were eager to start their own venture, always on the lookout for a winning business idea. Noticing that many small businesses struggled with mobile website creation, they dedicated their evenings and weekends to developing a solution. Eventually, they shipped basic software for building mobile websites. But they struggled to find customers because they had full-time jobs and not enough time to dedicate to their business. Getting investors on board was tough, too. Nearly every investor they spoke to wanted to see more customers and traction. And many were skeptical about the business idea. The first year was full of frustration and the founders questioned if they were on the right track. But the pair kept going, relentlessly improving their product and looking for customers. Eventually, they caught a lucky break when their product caught the attention of someone at AT&T, who reached out to learn more about what they were building. Three months later, they had signed a significant contract with AT&T. Today, Duda is an 8-figure ARR company used by 22,000 agencies to manage over 1 million websites. The team's grown to 180 and they've raised $96 million in funding.

Why SaaS Partnerships Work With Just Hundreds of Customers - Andrew Brown

Andrew Brown, Check

Why SaaS Partnerships Work With Just Hundreds of Customers

Andrew Brown is the founder and CEO of Check, a payroll infrastructure startup that embeds payroll directly into other software platforms. In 2015, Andrew sold his B2C startup, Oyster, to Google. But that big win also left a void in his professional life. He decided his next startup would be something he could work on for a decade or more, rather than just aiming for a quick sell-off. After spending years carefully searching for the right business idea, Andrew finally landed on the concept for Check when a potential partner revealed just how complex it was to build payroll functionality directly into their HR platform. Andrew spent several years operating in stealth mode, entirely focused on establishing Check's initial product and early partnerships before ever officially launching. But earning trust was much harder than Andrew expected, with many early prospects questioning why they should trust an early-stage startup with their payroll solution. It took years of relationship building through warm introductions, thoughtful cold outreach, and diligently preparing for every meeting to finally land pilots with initial partners. As Andrew described, payroll is an incredibly complex 50-state problem requiring going state-by-state to ensure proper setup before anyone will trust you with money. Today, Check has grown to a team of over 100 people and raised $119 million so far.

116 LinkedIn Conversations That Built an 8-Figure SaaS - Peter Ord

Peter Ord, GUIDEcx

116 LinkedIn Conversations That Built an 8-Figure SaaS

Peter Ord is the founder and CEO of GUIDEcx, a client onboarding and implementation platform. In 2017, Peter launched GUIDEcx. He had seen firsthand the problems with customer onboarding at his previous job and wanted to help companies make it better for their clients. He kicked things off by talking to more than 100 people who managed customer onboarding. He wanted to make sure there was a real need for specialized software. Once he was confident that there was, he put together an early version of the product to show to potential customers. In the beginning, Peter made some key decisions that set GUIDEcx on the path to success. For example, he raised his pricing pretty early on, which helped him attract customers who valued what he was offering and were willing to pay for it. But it wasn't all smooth sailing. During the first year, two important team members quit. They were half of his team back then and left because the business was growing too slowly. After losing those two people, Peter had an important decision to make. Was he going to build a lifestyle business and continue to grow slowly? Or was he going to go all-in, raise money, and build a fast-growing startup? He chose the latter. Today, GUIDEcx has hundreds of customers, has hit the $10 million ARR mark, and raised over $40 million.

How SaaS Content Marketing Built an 8-Figure Business - Dominik Angerer

Dominik Angerer, Storyblok

How SaaS Content Marketing Built an 8-Figure Business

Dominik Angerer is the co-founder and CEO of Storyblok, a headless content management system that helps developers and marketers create better content experiences. In 2017, Dominik and Alexander discovered the limitations of traditional CMS platforms while working at an agency. They needed a CMS that could be customized for client projects, but nothing on the market combined the flexibility of headless architecture with the visual editing experience marketers needed. So they built a prototype. That prototype grew in popularity. Brands like Adidas and Silhouette started using it. The two founders quit their agency jobs and launched Storyblok as its own company. Their SaaS content marketing strategy was unconventional. Instead of chasing high-volume keywords, Dominik and Alexander wrote long-tail technical tutorials - how to use Storyblok with PHP, React, Angular, Python, and every framework they could think of. Every article answered a question someone had already asked in their live chat. The result: they ranked #1 for "headless CMS explained" and hit 3,000 users within four months of launching the website. They bootstrapped for two and a half years, reaching $1M ARR with just the two of them. The entire customer base of 25,000 users came from SaaS content marketing and inbound. They only started outbound sales in mid-2022 - five years after founding. But it was not all smooth sailing. Enterprise prospects loved the product but walked away when they discovered it was a two-person company. The founders wasted three months building e-commerce and search tools instead of focusing on the CMS. And a missing letter in their domain name still costs Storyblok roughly $500,000 per year in paid ads to capture misspellings. Today, Storyblok is an eight-figure ARR business with 235 employees across 47 countries. They have raised $58 million in funding, earned Gartner Customer's Choice recognition, and Forrester calculated a 582% ROI for their customers. 70% of revenue comes from enterprise clients, with just 3% enterprise churn.

He Waited 10 Years to Launch - Then Grew 400% Year Over Year - Anshu Sharma

Anshu Sharma, Skyflow

He Waited 10 Years to Launch - Then Grew 400% Year Over Year

Anshu Sharma is the co-founder and CEO of Skyflow, a privacy API that acts as a data vault for sensitive customer information like Social Security numbers, credit cards, and health records. Before starting Skyflow, Anshu was a product manager at Salesforce and Oracle, where he spent over a decade watching companies struggle with the same data privacy problems. After 10 years of studying the problem across financial services, healthcare, and consumer tech, Anshu finally launched Skyflow in January 2019. But he took an unconventional SaaS go-to-market approach - he and his co-founder built the product for over 12 months without talking to a single customer. For a category-creating company like Skyflow, there was no MVP shortcut. The minimum viable product for a new data infrastructure layer had to be robust enough that a CTO could see why it was fundamentally different. The bet paid off. Skyflow's very first customer call ended in a sale. A former CTO of Goldman Sachs told Anshu it was the easiest buying decision of his career. Within a few years, Skyflow crossed seven-figure ARR, grew 400% year over year, hired 105 people, and raised $70 million through Series B. The SaaS go-to-market strategy that drove Skyflow past 100 customers was thought leadership content that educated the market from first principles - explaining why a data privacy vault needed to exist, rather than pitching features. Anshu also shares the story of a major customer who tried to cancel after a leadership change, and how turning that relationship around led to an even bigger deal years later.

2 Years of Discovery Before Writing a Line of Code - Brett Turner

Brett Turner, Trovata

2 Years of Discovery Before Writing a Line of Code

Brett Turner is the founder and CEO of Trovata, a fintech SaaS company that automates and simplifies cash management for businesses. In 2016, Brett, already a seasoned entrepreneur with three successful startup exits, launched a new endeavor. But this wasn't just another startup for him. It was an idea brewing for 20 years. Launching an enterprise SaaS product can be very challenging. So Brett spent over two years in the discovery phase talking to as many potential customers as he could. It was a long time, but he still felt it was worth it. However, one major obstacle stood in Brett's way. To deliver a successful product, he needed to integrate with banks. Back then, most didn't have APIs. So he made a huge bet. He was going to start building the product and investing in the business with the hope that banks would start providing APIs soon. If they didn't, he was screwed. The banks eventually introduced APIs, but Brett had to wait over 2 years. During that time, the pressure was growing as he was burning through cash. Thanks to that bet paying off, Trovata has grown into an enterprise SaaS business doing around $10M ARR with over 200 customers and has raised over $58 million. JP Morgan became their very first institutional investor after seeing Trovata connect to their corporate banking APIs before anyone else.

100 Interviews Before Code: Finding Product-Market Fit - Brandon Foo

Brandon Foo, Paragon

100 Interviews Before Code: Finding Product-Market Fit

Brandon Foo is a second-time founder who learned the hard way that building a great product means nothing if nobody needs it badly enough to pay. His first startup, Polymail, was an email productivity app that attracted tens of thousands of users but never found a large enough market to sustain growth. That experience taught Brandon a critical lesson about finding product-market fit: stop building and start selling. When Brandon and his co-founder Ishmael started Paragon, they flipped the playbook. Instead of spending months writing code, they ran over 100 customer interviews, showed mockups and prototypes, and asked prospects to enter their credit cards on a Stripe form for a product that barely existed. They started at $30 per month and gradually raised prices to test the ceiling of customer willingness to pay. That iterative approach to finding product-market fit led them through several pivots. Paragon started as a backend-as-a-service (similar to Firebase), but customer conversations kept pointing to one consistent pain point: building and maintaining SaaS integrations. Brandon and Ishmael followed the signal, refined the product, and eventually built an embedded integration platform that helps software companies connect with tools like Salesforce, Slack, and HubSpot. Today, Paragon serves over 100 customers, supports 90+ integrations out of the box, and has grown to several million dollars in ARR with a team of 30+. They raised $16 million in venture funding, including a $13 million Series A led by Inspired Capital. Brandon also shares how LinkedIn ads became Paragon's most successful growth channel, and the delegation challenges he faces scaling from a founder-led company to a team-driven organization.

11 Years Bootstrapped Then Funded to Build Enterprise SaaS - Neha Sampat

Neha Sampat, Contentstack

11 Years Bootstrapped Then Funded to Build Enterprise SaaS

Neha Sampat is the founder and CEO of Contentstack, a headless CMS that helps large enterprises manage and deliver digital content across websites, mobile apps, smartwatches, and more. Contentstack started life inside Raw Engineering, a digital services agency Neha founded after running the web store at VMware. In 2011, her team built a simple form that let clients edit mobile content without filing developer tickets. By 2014, Forrester named it one of three pioneers of headless CMS, and the enterprise SaaS opportunity became impossible to ignore. Neha bootstrapped the product for 11 years before spinning Contentstack out as a standalone company in January 2018. By then it had a couple dozen customers and was over $1M ARR. But raising capital as a first-time female founder who'd only run a services business proved harder than the metrics justified - only 3% of venture capital goes to female-led companies. She closed a convertible note in late 2018, then a large Series A in 2019 at a high valuation. Today Contentstack has raised $169 million through its Series C, grown to 450 employees across 18 countries, and serves Fortune 1000 brands including Chase, Asics, Holiday Inn, and Mattel. The enterprise SaaS contracts that once started at $250 a month now reach $1 million or more per year. We talk about how inbound worked from day one because Contentstack was one of the first websites with "headless CMS" in the header during a wave of cloud adoption, mobile, and SaaS. We discuss the shift to outbound BDR teams and account-based marketing, the partner ecosystem that became critical for enterprise SaaS deals, and why Neha's biggest regret is not raising capital sooner - not because she was stubborn about equity, but because she simply didn't know it was an option.

Scaling SaaS With Unit Economics, Not Just Growth - Vishal Sunak

Vishal Sunak, LinkSquares

Scaling SaaS With Unit Economics, Not Just Growth

LinkSquares CEO Vishal Sunak first appeared on the podcast in 2021, when his contract management platform was doing $10M in ARR with a team of 70. Two years later, the numbers tell a scaling SaaS story that few founders experience: $40M ARR, $161M raised, an $800M valuation, and over 430 employees. The growth did not come from luck. Vishal and his leadership team built a go-to-market predictability engine that starts planning a year in advance, scrubs customer data obsessively, and doubles down on the verticals and company sizes where close rates are highest. When a segment closes at 50%, they flood it with demos. When 24 attempts in a segment produce zero wins, they stop wasting rep time. Scaling SaaS beyond $10M also required a shift to unit economics rigor. Vishal's CFO and finance team now forecast cost of goods sold for an entire year. They track CAC payback, burn multiple, gross margin, and ARR per rep productivity - and they use that data to make every hiring and spending decision. The episode also covers the painful side of scaling SaaS at this pace: growing from 70 to 430 people in two years while building career laddering, performance review cycles, equitable compensation, and systematized onboarding. Vishal describes how his role evolved from being the person who did everything - cold emails, security questionnaires, deal desk - to a CEO whose only job is making the hardest decisions and thinking about what comes next.

The SaaS Go-to-Market Playbook That Signed 250 Customers - Roxanne Petraeus

Roxanne Petraeus, Ethena

The SaaS Go-to-Market Playbook That Signed 250 Customers

Roxanne Petraeus spent seven years as an army officer before joining McKinsey. On her first day of compliance training at one of the world's best consulting firms, she was stunned by how terrible the software was. That moment sparked the idea for Ethena. In 2019, Roxanne met her co-founder and CTO, Ann, through a serendipitous introduction. Three weeks later they launched a beta. Roxanne had already interviewed HR leaders at over 30 companies to understand why compliance training was so universally hated. The answer was consistent: it was painful to administer, employees despised it, and the software constantly broke. Their SaaS go-to-market strategy was unconventional. Instead of outbound sales or paid ads, Roxanne partnered with a VC fund's HR leader who shared Ethena's free beta with 50 portfolio companies. That distribution hack gave them their first cohort of customers. Then a TechCrunch article about fixing broken compliance training caught the eye of Netflix's CEO, who forwarded it to his legal team. Word of mouth took over from there. Today Ethena serves almost 100,000 employees across 250 customers including Netflix, Zendesk, Figma, Notion, and Superhuman. The company has raised just over $50 million. Roxanne also shares hard-won lessons from her SaaS go-to-market journey - how she learned to sell without domain expertise, why pitching execution over vision cost her early fundraising rounds, and how two women founders navigated bias in venture capital while building a seven-figure SaaS business.

From Zero Sales Skills to Founder-Led Sales Machine - Nik Mijic

Nik Mijic, Matik

From Zero Sales Skills to Founder-Led Sales Machine

Nik Mijic is the co-founder and CEO of Matik, a SaaS product that automates data-driven presentations in PowerPoint and Google Slides. Before starting Matik, Nik worked as a program manager at LinkedIn, where he built internal tools that helped sales and customer success teams create data-heavy decks. In 2018, Nik realized that many B2B companies were wasting hours manually pulling data from Salesforce, Tableau, and other sources just to build quarterly business reviews and ROI decks. He saw an opportunity to automate the entire process. But he wasn't ready to quit his job just yet. Nik met his co-founder Zach through a mutual friend. Zach was an early engineer at Box who had stayed through the IPO. The two spent five to six months researching the idea, validating the problem with potential customers, and making sure they were a good fit for each other before committing. When Nik finally decided to leave LinkedIn, the hardest part was telling his parents. As refugees from the Bosnian civil war, they had sacrificed everything to give their children opportunities in the US. But instead of pushing back, they told him to go for it - even offering to sell their house if he needed support. The co-founders started working out of Nik's apartment in early 2019. Building the product came together quickly, but selling it was a different story. Neither Nik nor Zach had any sales background. Nik's founder-led sales approach started at a dinner party, where a woman introduced him to her company's enablement team. They loved the prototype, asked where to sign, and Nik realized he didn't even have a purchase order or legal terms. He made up a price of $2,500 on the spot, and that became Matik's first paying customer. From there, Nik leaned heavily on his LinkedIn network and a clever tactic: reaching out to former LinkedIn employees who had moved to new companies and missed the internal tools Nik had built. That approach got Matik to its first 15 to 20 customers. When it came time to build a sales team, Nik learned a key lesson: hire in twos. Bringing on two account executives or two SDRs at the same time lets you benchmark performance and figure out whether issues are with the person or the process. He also discovered that founders never fully step away from selling - even after hiring a head of sales, Nik stayed involved in deals to keep a pulse on the market. Today, Matik's customers include B2B tech companies like Asana, Glassdoor, Greenhouse, and SalesLoft. The founders have raised $23 million, including a $20 million Series A from Andreessen Horowitz.

How a Tech Founder Used Founder-Led Sales to Hit $1M ARR - Hung Dang

Hung Dang, Y42

How a Tech Founder Used Founder-Led Sales to Hit $1M ARR

Hung Dang is the founder and CEO of Y42, a fully managed DataOps cloud that helps companies design production-ready data pipelines on top of their Google BigQuery or Snowflake data warehouse. After years working in data analytics and running an event analytics company that was acquired by a German Fortune 100 company, Hung became frustrated with the five-plus tools needed to build a proper data infrastructure. In 2020, he decided to build an end-to-end data platform to replace them all. But Hung didn't interview customers to validate his idea. He hired a team of engineers and spent a full year building the product in silence. When he finally put it in front of customers, he discovered it was missing about 30% of the features they needed, and about 20% of what he built was not important to them. Despite that rocky start, Hung used founder-led sales to close Y42's first customers through angel investor networks and vision selling. The company hit $1M ARR within a year of launching. Hung talks about how his early experience doing door-to-door donations for the Red Cross taught him resilience and sales fundamentals that carried over into founder-led sales as a tech CEO. Y42 has since raised $34 million in funding, grown to 150 employees, and serves hundreds of customers across e-commerce, retail, and B2B SaaS. Hung shares the lessons he learned about balancing product building with customer conversations, why hiring senior sales and marketing leaders took over 10 months, and how thought leadership on LinkedIn became a key growth channel for a data infrastructure company.

How Attest Got Customers to Call VCs and Raise Funding - Jeremy King

Jeremy King, Attest

How Attest Got Customers to Call VCs and Raise Funding

Jeremy King spent nine years as a McKinsey consultant watching companies guess what consumers wanted instead of using data. In 2015, he decided to fix that problem by building Attest, a consumer research platform that lets B2C companies survey over 125 million people in 58 countries starting in 90 seconds. But his wife gave him just six months to get the business going. So Jeremy had to compress what normally takes two years of startup grinding into a fraction of that time. His SaaS fundraising approach was unconventional. He split 15 potential customers into three groups - five he knew well, five he had loose connections to, and five he cold-contacted, including American Express and Expedia. He asked them all one question: what data do you wish you had about your customers that you don't have today? Then he got those companies to call seed VCs and say "please invest in this company so I can buy their product." But Jeremy's SaaS fundraising playbook went further. He deliberately pitched Series B and C investors, knowing they couldn't write a seed check. They gave him feedback on his long-term pitch, told him the milestones they'd want to see, and then referred him to their favorite seed VCs. Those seed funds then received two calls - one from a Series B investor and one from a customer - both saying "fund this company." After raising 650,000 pounds in September 2015, Jeremy and his co-founder Tony Hunter built the product with internationalization baked in from day one. In November 2017, they flipped every user from pay-as-you-go to annual subscriptions. Most converted, and through referrals and vision-aligned selling, Attest hit $1M ARR in 7.5 months. Today, Attest generates eight figures in ARR, employs around 170 people, and has raised $104 million in total SaaS fundraising. Jeremy also shares why their freemium experiment bombed, how they compete against guesswork instead of incumbents, and why he'd never heard the term "SDR" until 18 months after first revenue.

Scaling SaaS by Failing Upmarket First - Christian Owens

Christian Owens, Paddle

Scaling SaaS by Failing Upmarket First

Christian Owens started building websites when he was 12 years old, walking into local businesses and offering to build them a site. His first customer was an Indian restaurant. By 14, he had convinced software vendors to participate in discounted bundles and generated over $1 million in gross sales from a combined email list of 250,000 subscribers - without having a single subscriber of his own on day one. The pain of running that high-volume software business - handling payments through PayPal, fighting fraud, managing sales tax across dozens of countries - led Christian to found Paddle at 18 years old. He built it to be the product he wished had existed: one platform that handles payments, subscriptions, billing, invoicing, and tax compliance for SaaS companies. The first version of Paddle was actually a software marketplace. It flopped. But customers kept asking for the commerce engine behind it - the checkout, recurring billing, and payments infrastructure. That pivot defined the business and set the stage for scaling SaaS payments across thousands of companies. Scaling SaaS from $10M to $100M in ARR required Paddle to move upmarket. The first attempt failed badly. Christian hired experienced enterprise account executives, pointed them at large logos, and assumed the same value proposition that won $1M customers would work on $50M prospects. Every sales rep quit within six to nine months. The second attempt worked because the team rebuilt ROI messaging, added enterprise product features like 2FA and audit logs, and learned to articulate value at the buyer's current scale instead of the scale they were at when they first signed up. Today Paddle employs nearly 400 people, has raised $300 million in venture capital at a $1.4 billion valuation, and counts Verizon, Fortinet, and ServiceNow among its enterprise customers. Christian also led the acquisition of ProfitWell for $200 million, combining Paddle's payments infrastructure with ProfitWell's retention and metrics tools - a deal that reflects the compounding effect of scaling SaaS by solving adjacent problems under one roof.

She Gave Her SaaS Away Free for 18 Months. Here's What Changed. - Cristina Vila

Cristina Vila, Cledara

She Gave Her SaaS Away Free for 18 Months. Here's What Changed.

Cristina Vila is the co-founder and CEO of Cledara, a product that helps companies simplify the way they discover, buy, manage and cancel subscription software. In 2018, Cristina quit her job to start her SaaS business. She was a first-time founder, who didn't know how to code and didn't have any sales experience. But she was driven by a life-long dream to one day start her own business. After raising a pre-seed round, she hired a software development company to build the product which she launched at SaaStock in Dublin three months later. But when she tried to sell her product, she got a lot of objections. Some people said that they didn't have a problem managing software subscriptions, others felt they already had a good solution in place (even if it was just a spreadsheet), and a lot of other people just weren't interested at that time. So for a while, things weren't looking good for Cristina. And even worse, she didn't charge for her product for 18 months. In fact, there wasn't even a way for customers to pay for her product - which many would say was a rookie mistake. Despite those challenges, Cristina and her co-founder Brad, have grown Cledara to $2.4M in ARR so far with over 700 customers. And they've raised $7M and built a team of nearly 50 people.

3 Years of Zero Traction Then Finding Product-Market Fit - Khadim Batti

Khadim Batti, Whatfix

3 Years of Zero Traction Then Finding Product-Market Fit

Khadim Batti is the co-founder and CEO of Whatfix, a Digital Adoption Platform (DAP) that helps businesses simplify training and support. In 2014, Khadim and his co-founder Vara launched a new SaaS business called Whatfix. In 8 years, they've grown their company to multiple 8-figures in ARR, hired over 600 employees, and they've raised $140 million in VC funding. It sounds like another great Silicon Valley startup story, but it isn't. Both these founders were based in India. Prior to founding Whatfix, they spent 3 years building another product that never really got traction. Both founders came from an engineering background, so they spent too much time trying to build a great product and not enough time talking to customers. During those 3 years, there were many times when they wanted to quit and go back to their corporate jobs. At one point, they realized that there was one feature in their product that their customers seemed to be most interested in. In fact, it wasn't even a product feature, but a tool they'd built to help their customers learn how to use their product. So they decided to shut down the product they'd been working on for 3 years and instead focus on turning that tool into a product. But this time they took a very different approach. They spent most of their time talking to customers and validating their idea. And they didn't start building the product until they'd made their first sale. In this interview, Khadim shares his lessons on the mistakes they made in building their first product. And we dig into how they took a very different approach the second time with Whatfix, and how they've gone from zero to a company valued at over $600 million. I hope you enjoy it.

5 Capital Raising Mistakes That Kill SaaS Fundraising - Brian Parks

Brian Parks, Bigfoot Capital

5 Capital Raising Mistakes That Kill SaaS Fundraising

Brian Parks is the founder and managing partner of Bigfoot Capital, a company that provides non-dilutive growth capital to B2B SaaS companies. Since 2017, Bigfoot has funded about 35 companies, typically investing $500K to $2.5M into businesses with $1.5M to $10M in ARR. Brian has a unique perspective on SaaS fundraising. He was an investment banker, then raised equity as a startup founder at Brandfolder, and now he raises money for Bigfoot Capital while also deploying it into early-stage SaaS companies. He recently raised $30M for Bigfoot in a process that took about 15 months. In this conversation, Brian walks through the 5 most common capital raising mistakes he sees SaaS founders make - from conducting a "casual raise" to going after the wrong audience to over-optimizing term sheets. He also shares an 8-step fundraising process that covers everything from discovery and outreach to diligence and closing. Whether you are raising your first round or thinking about non-dilutive alternatives to venture capital, this episode gives you a practical framework for running a tighter, faster, more effective SaaS fundraising process.

From Teen Side Project to SaaS Fundraising Win - Liam Gerada

Liam Gerada, Krepling

From Teen Side Project to SaaS Fundraising Win

Liam Gerada is the co-founder and CEO of Krepling, an e-commerce platform for online stores. In 2018, two teenage brothers in Malta wanted to start an agency. They had recently sold their Shopify store and decided that they wanted to help others running similar businesses. They spent a few months validating the idea but realized people did not need an agency - they needed a better platform. So Liam and Travis set out to build a Shopify competitor. Neither of them was a developer, but Travis had taken some courses so he knew just enough to start building something. After months of work, they shipped a product with a clunky backend and an ugly user interface. But the product was free and they were still able to attract new users. But as soon as they started charging, every user they had churned. The brothers pushed on and tried anything they could think of to find customers - posting on sites like Quora and Reddit, sending cold emails. Eventually, they were able to find a handful of customers. Fast forward to today. Liam is now 21 and Travis is 18. The two brothers have made significant improvements to their product. They now have over 500 customers and they have raised a pre-seed round from Jason Calacanis' LAUNCH accelerator. They still have a long way to go and a lot more work to do, but they have accomplished a lot in the last couple of years. They are both still pretty young, did not have tons of experience, did not know how to code, and live on a small island in the middle of the Mediterranean. But that has not stopped them from building their SaaS business and securing SaaS fundraising to take Krepling to the next level.

SaaS Fundraising: From Bootstrapped to 1.2M in 18 Months - Holly Stephens

Holly Stephens, Subly

SaaS Fundraising: From Bootstrapped to 1.2M in 18 Months

Holly Stephens is the co-founder and CEO of Subly, a SaaS product that provides automatic transcription, translation, and subtitles for audio and video content. When Holly was running an online community and marketing agency, she realized how effective video was in attracting customers for both herself and her clients. But she quickly discovered how difficult it was to create subtitles and transcriptions for those videos and then share them across various platforms. Holly wondered if this was also a big pain for other content creators and if there might be an opportunity for her to solve that problem. She knew that the best way to move forward with an idea was to just get it out there and see what happens. So she quickly created a landing page. The page was pretty simple. It described a fictional product that would make it easier to add subtitles to videos and invited people to signup and get notified when it launched. She shared the link to the landing page in different Facebook groups and in a few days, about fifty people signed up. That was enough for Holly and her co-founder Keyvan to move ahead with the idea. For the next year, they still worked their day jobs but would meet in the mornings and evenings to work on their product. Eventually, about a year later they launched their product and had around a hundred people signup. But the product was still free and they hadn't yet figured out how to make money. And it took them several more months to figure out how to get their first paid customer. Currently, Subly is doing around $120K in annual recurring revenue, the team has raised a seed round and have around 60,000 people using the product.

SaaS Fundraising: How a No-Name Founder Got Funded - Vishal Sunak

Vishal Sunak, LinkSquares

SaaS Fundraising: How a No-Name Founder Got Funded

Vishal Sunak is the co-founder and CEO of LinkSquares, a contract management solution for in-house legal teams to draft, store, search, and analyze agreements. In 2015, Vishal was working at Backupify which was about to get acquired. The acquiring company wanted to know what was in their customer agreements. But Backupify had thousands of different customer agreements. No one knew what was in them and there was no easy way to get that information. That first-hand experience of contract management and the pain points in-house legal teams face planted a seed in Vishal's mind of a potential SaaS solution. Eventually, Vishal and his two co-founders (Chris Combs and Steve Travaglini) took the leap and launched their startup to revolutionize contract management. They built a Ruby on Rails MVP with no backend. In other words, it was good enough to use for demos but wasn't a product that customers could use. The founders then spent 9 months interviewing nearly a hundred general counsels. And it took them over a year to land their first few customers. Vishal was worried about building the wrong product and wasting their money. So they wanted to be sure they were solving the right problem. Today, LinkSquares does $10 million in annual recurring revenue (ARR), has a team of 70 people, and has raised over $21 million in funding.

5 Days From Shutdown to SaaS Pivot That Found PMF - Romain Dardour

Romain Dardour, Hull

5 Days From Shutdown to SaaS Pivot That Found PMF

Romain Dardour is the co-founder and CEO of Hull, a SaaS product that collects, unifies, and enriches your product, marketing, and sales data and synchronizes it to all of your tools. In 2011, Romain was running a marketing agency in Paris. He was working with movie studios that wanted him to rebuild online communities from scratch for every new movie launch. He realized that there was a more efficient way to solve that problem and decided to build a product. And for the next 4 years, he and his co-founders struggled to find product-market fit. In 2016, after trying to unsuccessfully bootstrap the business for 4 years, they decided that the market just wasn't there and that it was time to move on. They made the decision to shut down the company. Around the same time, Romain had lunch with a growth marketer friend who wasn't interested in the product but liked how they were collecting and segmenting data. He thought that would be something a lot of companies would be interested in. So in the next 5 days, Romain and his co-founders built a prototype and started getting feedback. And that's how the idea for their new product was born. They went from being a month away from shutting down their company to finding a new opportunity which they pounced on and pivoted the business. Today, they charge at least $1,000 a month for their product and have around 100 customers. They've raised $5M in funding and have found product-market fit. In this interview, we talk about how they struggled in the first few years, how they turned a lunch meeting into a new product idea, and how they've grown their business.

Startup Funding Without Giving Up Equity or a Pitch Deck - BJ Lackland

BJ Lackland, Lighter Capital

Startup Funding Without Giving Up Equity or a Pitch Deck

BJ Lackland is CEO of Lighter Capital, a Seattle-based company that specializes in providing financial capital to early-stage SaaS companies through revenue-based financing. Raising startup funding is painful. It takes months, requires endless pitches, and often means giving up a significant chunk of your company. But what if there was a way to raise $50,000 to $3 million without diluting your ownership, without providing personal guarantees, and without ever doing a traditional pitch? That is exactly what Lighter Capital offers. When BJ joined the company in 2012, it had three employees and no real revenue model. He refocused the business on SaaS companies, built a tech-enabled underwriting platform that analyzes 6,500 data points per company, and grew the team to 65 employees. Lighter Capital has now provided over $155 million in startup funding across 560 rounds to 318 companies. Revenue-based startup funding works differently from equity or debt. Lighter Capital provides a loan and takes a percentage of monthly revenue - typically around 5% - until the founder has paid back about 1.4x the original amount. If the company grows faster, Lighter Capital earns a higher return. If growth slows, payments automatically decrease. No board seats. No equity. No personal guarantee. BJ also shares how he turned the company around by focusing on a beachhead market of SaaS companies, building a partnership with Salesforce that drove 25% of deal flow, and simplifying the product to make startup funding accessible through a process that takes about 10 hours of the founder's time. Whether you are generating $15K MRR and looking for growth capital or weighing your startup funding options between equity and debt, this conversation breaks down a path most founders overlook.

SaaS Fundraising 101 from Pre-Seed to Series A - Elizabeth Yin

Elizabeth Yin, Hustle Fund

SaaS Fundraising 101 from Pre-Seed to Series A

Elizabeth Yin is the co-founder and general partner at Hustle Fund - the seed fund for hilariously early hustlers. She's also the co-founder of Hustle Con, a conference for non-technical startup entrepreneurs. Previously, Elizabeth founded LaunchBit, which was acquired in 2014. She was also a partner at 500 Startups where she led the accelerator program. In this interview we cover SaaS fundraising 101 for early-stage startups. So if you are thinking of fundraising but don't know where to start, this episode will help you figure that out. We talk about the fundraising landscape and the differences between pre-seed, seed, and post-seed stages. Elizabeth shares advice on how to approach investors, how to set up meetings, the do's and don'ts of pitching to an investor, how to think about valuation of your startup, and how to choose the right investor for your SaaS fundraising round. It's an episode jam-packed with actionable insights. I hope you enjoy it.

SaaS Fundraising: 100 Investor Meetings for One Round - Kelsey Recht

Kelsey Recht, VenueBook

SaaS Fundraising: 100 Investor Meetings for One Round

Kelsey Recht is the founder and CEO of VenueBook, a booking platform that connects event planners with venue managers. VenueBook helps venues to manage their leads and bookings, and market their space. And it helps event planners to easily find and book the right venue for their event. VenueBook was founded in 2010 and is based in New York. The company has raised over $9 million in funding. Kelsey is a first-time SaaS founder who came up with the idea for this business after experiencing the pain of finding venues and booking events herself. And one of the smart things that she did in the early days was not to start building a software product right away, but going out and talking to prospective customers about their pains. In fact, that's how she found her first few customers and her first developer. The SaaS fundraising journey was particularly challenging. Although Kelsey has raised over $9 million, it was far from easy. She started with a small friends and family round to get the business started, but raising a seed round was seriously hard work. She had to go out and talk to over 100 investors before she was able to get her seed round together. The Series A was a different story - investors said yes or no quickly, making it a much more efficient SaaS fundraising process. We talk about the lessons she has learned as a SaaS entrepreneur, as a first-time founder, and as a female entrepreneur.

$6.5M Raised, Zero Traction: A Failed Software Startup Story - Mike Muhney

Mike Muhney, VIP Orbit

$6.5M Raised, Zero Traction: A Failed Software Startup Story

Mike Muhney is the founder and CEO of VIP Orbit, a software company focused on building great contact management products. He launched their flagship product VIP Orbit in 2010 and they raised $6.5 million. Recently, Mike had to shut down the business because he ran out of money and was not getting the traction that he had hoped for. So in this episode, he joins me to talk about the lessons he has learned from a failed software startup. We have a very open and candid conversation about what he thinks led to that failure. Mike was in a similar situation in the 1980s when he co-founded a startup which eventually failed. He had raised $100,000 from an angel investor. He ended up with $15,000 of that money left and needed to give back the money or come up with another idea. And he and his co-founder came up with ACT contact management software, which they went on to sell for $47 million. So Mike is a seasoned entrepreneur who has seen the highs and lows. In this episode, he is willing to talk about the tough parts of being an entrepreneur and what led to his failed software startup.

This Vertical SaaS Replaced a 120-Year-Old Eye Exam - Aaron Dallek

Aaron Dallek, Opternative

This Vertical SaaS Replaced a 120-Year-Old Eye Exam

Aaron Dallek is a serial entrepreneur who started his first business at 14. His co-founder, Dr. Steven Lee, was an optometrist who had performed 20,000 refractions when a patient asked a simple question: "Why can't we do this at home?" That question became the foundation for Opternative, a vertical SaaS that fundamentally changed how eye exams work. The two co-founders self-funded the initial proof of concept, then spent two and a half years building and validating a technology that uses a computer screen and smartphone to identify refractive error - no lenses required. They ran 1,500 refractions comparing their digital method against traditional exams and proved statistical equivalency in a clinical trial. Opternative grew to over 100,000 signups, partnered with 1-800 Contacts, and raised $9.5 million across seed and Series A rounds. The product charges $40 for a glasses prescription and $60 for both glasses and contacts, with a refund rate of just 0.06%. But building a vertical SaaS in healthcare comes with unique obstacles. While the ophthalmology community supported the technology, optometry trade groups pushed legislation in multiple states trying to ban or restrict online eye exams. Aaron shares how Opternative navigated regulatory pushback, why everything takes longer than you expect, and how tenacity from overcoming a childhood learning disability shaped his approach to entrepreneurship.

Bootstrapped 7 Years Then Skipped VCs in SaaS Fundraising - Pini Yakuel

Pini Yakuel, Optimove

Bootstrapped 7 Years Then Skipped VCs in SaaS Fundraising

Pini Yakuel and his co-founder met while studying at Tel Aviv University. They knew they wanted to apply machine learning to a real business problem, but they had no product idea, no coding ability, and no capital. They spent months meeting with companies to understand their data challenges before landing on predictive customer modeling for marketing. Unable to build software themselves, they started a consulting business to generate revenue. A $30,000 government grant helped them outsource the first version of their product. For the next several years, they used consulting income to fund development and hire engineers, turning Optimove into a SaaS platform that predicts customer behavior across the entire lifecycle. In 2012, a VC offered $1.5 million, and Pini turned it down. He felt the company's identity was still forming and that VC pressure to grow faster than the business was ready for would destroy the culture. Optimove continued growing 100% year over year organically, reinvesting every dollar back into the business. Seven years after founding, Pini finally pursued SaaS fundraising - but with a growth fund, not a VC. By then, Optimove had over 100 employees, offices in Tel Aviv, New York, and London, and a mature product with real enterprise customers. The $20M round was raised from a position of strength, not desperation. Pini shares why SaaS fundraising timing matters more than fundraising itself, how consulting-to-SaaS transitions build stronger products, and why founders who can sell have a massive advantage over all-technical teams.

From Evernote Idea to SaaS Product-Market Fit - Zvi Band

Zvi Band, Contactually

From Evernote Idea to SaaS Product-Market Fit

Zvi Band is the co-founder and CEO of Contactually, a CRM tool that helps professionals stay engaged with their most important relationships. He founded Contactually in 2011 after writing down an idea for a "proactive CRM" in Evernote. What started as a weekend prototype built by one of his engineers grew into a company with over 70 employees and more than $12 million in venture funding. The company is based in Washington, D.C., and generates several million dollars in annual revenue on its way toward $10 million ARR. Zvi's path to SaaS product-market fit was anything but smooth. The first product version sent annoying emails asking users to categorize every new contact - people hated it. The second version reminded users to follow up with everyone, including people they did not care about. It was only after multiple rounds of customer development that the team discovered the key insight: users wanted to segment their relationships into buckets and only stay in touch with the people who mattered most. Before going full time on Contactually, Zvi ran a consulting firm and treated the product as a side project. When 500 Startups offered $50K to join their accelerator, it became a burn-the-boats moment - Zvi shut down his consulting business and his co-founder quit his job at Microsoft. In this conversation, Zvi talks about how he validated demand using lean pricing tests before charging customers, why SaaS product-market fit came from listening to user complaints rather than building more features, and the one thing he wishes he had done differently from day one.

How to Pitch Investors and Get Startup Funding - Judy Robinett

Judy Robinett, JudyRobinett.com

How to Pitch Investors and Get Startup Funding

Judy Robinett is the author of the book How to Be a Power Connector: The 5+50+100 Rule for Turning Your Business Network into Profits. In her 30 years of experience as an entrepreneur and corporate leader, she served as the CEO of both public and private companies. She has been on the advisory board of several venture capital firms and was the managing director of Golden Seeds Angel Network, one of the largest angel investment groups in the US. Judy has been profiled in Fast Company, Forbes, VentureBeat, Huffington Post, and Bloomberg Businessweek as an example of a new breed of power connectors. In this conversation, Judy breaks down how founders can build strategic networks to access startup funding - even if they consider themselves introverts. She explains the 5+50+100 framework for organizing relationships, shares the two questions that unlock hidden connections, and walks through what angel investors and VCs actually look for in a pitch. The conversation covers common mistakes founders make when pitching, how to de-risk your deal in an investor's eyes, and why beginning with the exit in mind changes how investors evaluate your startup funding potential.

A Simpler SaaS Go-to-Market That Replaced Every Demo - Alexandra Keating

Alexandra Keating, DWNLD

A Simpler SaaS Go-to-Market That Replaced Every Demo

Alexandra Keating is the co-founder and CEO of DWNLD, a mobile app platform that enables media companies, brands, and influencers to easily and affordably create beautiful, native mobile apps. Before DWNLD, Alexandra sold her first tech company - a charity platform called Go Fundraise - at the age of 19. After that experience, she swore she would never build another startup. But a decade later, while working at Thrillist Media Group, she noticed that every company was rebuilding the same mobile technology from scratch. The frustration became too much to ignore. Alexandra and her co-founder Fritz initially went deep on building a complex content management system. It was a mistake that cost them months. The breakthrough came when Alexandra decided to radically simplify the go-to-market approach: just give DWNLD a URL, and the platform spins up a native app in minutes. The simplification did not stop at the product. To acquire early customers without spending a dollar on marketing, Alexandra started cold emailing prospects with pre-built screenshots of what their app could look like - letting people experience the product before they even knew the company existed. That approach opened the floodgates. DWNLD has raised $14 million to date and serves over 3,000 content creators, helping them monetize through advertising, premium content, and commerce. The company is based in New York.

Launching a Marketplace for Algorithms With 14K Devs - Diego Oppenheimer

Diego Oppenheimer, Algorithmia

Launching a Marketplace for Algorithms With 14K Devs

Diego Oppenheimer is the co-founder and CEO of Algorithmia, a Seattle-based marketplace that connects academics building algorithms with app developers who need them. The company was founded in 2013 and raised $2.5 million in funding. The idea of launching a marketplace for algorithms started during a backpacking trip through Australia and New Zealand in 2008. Diego and his co-founder Kenny Daniel had been friends since college, and they spent months in a tent with a notebook and laptop, mapping out what a computation marketplace could look like. It took another five years of refining the concept before they launched. The real validation came from Diego's time at Microsoft. While building features for Excel, his team needed an advanced algorithm. After months of searching Microsoft Research - a $7 billion operation - he found that the exact algorithm he needed had already been built and was sitting inside Excel. Nobody knew. That failure to connect research with product teams, even inside one of the best companies in the world, confirmed that launching a marketplace to bridge that gap was a real opportunity. When it came time to raise money, Diego used his Excel skills to build a spreadsheet rating 60 investors by fit, location, interest, and portfolio overlap. Then he flipped the list and started pitching from the bottom - worst fit first. The logic: his pitch would be terrible early on, so he would learn from the investors least likely to fund him. By the time he reached the top of the list, he had answers to every hard question. The strategy worked, and they closed $2.5 million. Today Algorithmia has a team of nine, over 14,000 developers on the platform, and partnerships with universities. Diego talks about doing things that don't scale in the early days, the shift from internal product building to external evangelism, and the biggest lesson he learned transitioning from a company like Microsoft to startup speed.

9 Months With Zero Startup Funding Built a 100M-User App - Chris Barton

Chris Barton, Shazam

9 Months With Zero Startup Funding Built a 100M-User App

Chris Barton is the co-founder of Shazam, the mobile music recognition service that started as an idea in 1999. Every expert in audio signal processing told him and his co-founders that identifying music from noisy phone audio was impossible. They did it anyway. Chris and his team spent their first 9 months with zero startup funding, focused entirely on finding the right technical co-founder and inventing the core algorithm. They recruited Avery Wang by networking through Stanford and MIT PhD programs in signal processing. Once they had a working demo and a patent, they raised close to $1 million from angel investors, followed by a $7.5 million Series A. But building Shazam in 2000-2002 meant building everything from scratch. There were no cloud servers, no digital music databases, and no smartphones. Users would dial a phone number, hold their phone up to the music, and receive an SMS with the song name. Growth was slow for years. The real breakthrough came in 2008 when Apple launched the App Store. Shazam shot to the top of the charts and never left, eventually reaching over 100 million monthly active users. Chris shares the fundraising strategy that worked, the biggest mistake he made as a first-time CEO, and why he stepped down to let an experienced operator take the helm.

How Blogging 5 Nights a Week Built a $29M SaaS - Rand Fishkin

Rand Fishkin, Moz

How Blogging 5 Nights a Week Built a $29M SaaS

Rand Fishkin co-founded Moz (originally SEOmoz) in 2004 as a consulting firm he ran with his mother. At the time, the company was drowning in $500,000 of credit card debt, all in Rand's name so his father wouldn't find out. The turning point was SaaS content marketing. Rand forced himself to write blog posts five nights a week, often from 10pm to 2am, for five straight years. The content demystified how Google's search algorithm worked and attracted a massive audience of digital marketers who trusted him. When a developer named Matt Inman (who later created The Oatmeal) built some hacky internal SEO tools, they put them online with a PayPal button. No business plan, no scalability testing, no customer personas. The tools broke every couple of weeks and could only handle a few hundred users. But the audience was already there. The community of marketers who had been reading Rand's content for three years became instant customers. Moz doubled revenue every year for six years, reaching $29M in 2013. They raised $1.1M in 2007 and $18M in 2012 from Ignition Partners and Curious Office. Then growth stalled. Revenue growth dropped from 100% to 50% to just 6%. Rand was dealing with depression and openly admits he would spend five minutes convincing anyone who complimented Moz that their product was terrible. He stepped down as CEO, handing the role to Sarah Bird, because he recognized he was dragging the company down during a period when they needed an optimist at the helm.

800K Users in One Year With Product-Led Growth - Melanie Perkins

Melanie Perkins, Canva

800K Users in One Year With Product-Led Growth

Melanie Perkins came up with the idea for Canva while teaching design programs at university in Perth, Australia. The tools were so difficult to use that she saw a future where design would be entirely different - simple, drag-and-drop, and accessible to everyone. But turning that vision into reality took years. Melanie first built Fusion Books, an online yearbook design platform, with her co-founder Cliff Obrecht. They bootstrapped it from scratch, reinvesting profits each year. That product-led growth experience gave her five years of product and business knowledge before she ever pursued venture capital. When customers started asking if they could use Fusion Books for marketing materials and social media, Melanie knew the broader market was ready. She flew to San Francisco, spent three months learning about startups and investment, and eventually found her technical co-founder Cameron Adams. After raising $6 million in VC funding, Canva launched in 2013 and hit 800,000 users in its first year. The product-led growth strategy was deliberate. Melanie targeted bloggers and social media marketers first - people who needed to design daily and had large audiences. When bloggers started using Canva, they blogged about it. That created a viral loop where the product essentially marketed itself. Canva also introduced a patented $1 stock image license, making professional imagery affordable for everyday creators. By the time of this interview, Canva had 5.5 million designs created - with 1 million of those in the last month alone. The team had grown from 10 to 40 people in a single year, and Guy Kawasaki had joined as chief evangelist after tweeting a Canva design and being recruited directly by the team.

6,000 Customers Through Product-Led Growth - Andrew Filev

Andrew Filev, Wrike

6,000 Customers Through Product-Led Growth

Andrew Filev started his first company at 17. By his early twenties, he was running a multinational software consulting firm with hundreds of employees across multiple countries. But the rapid growth exposed a painful problem: the tools his team relied on - email, spreadsheets, and legacy enterprise software - could not keep up. He tried every collaboration and project management tool on the market. None of them worked. Work management and collaboration were treated as separate markets, but Andrew saw them as two sides of the same coin. That insight became the foundation of Wrike. Andrew self-funded the initial build, shipped a beta in under a year, and launched it at a conference. He made a deliberate choice not to lean on friends and family for early customers. Instead, he put Wrike online and let the product speak for itself. Strangers found it, tried it, and started paying for it. Wrike's product-led growth strategy combined a freemium model with content marketing and search engine marketing. The team knew nothing about marketing when they started, so they taught themselves. Trade shows failed. Analyst outreach fell flat while they were small. But content marketing and online channels scaled consistently. Today Wrike has more than 6,000 paying customers in over 50 countries, more than 40 Fortune 1000 companies on the platform, and has raised over $11 million in funding. The product scales from five-user teams to organizations with more than a thousand users managing thousands of projects. Andrew shares why his biggest mistake was not talking to customers enough, how he used a product-led growth approach to land enterprise accounts without an enterprise sales team, and why staying focused is the most important advice he ever received.

50K Day-One Users With Zero Marketing Spend - Sahil Lavingia

Sahil Lavingia, Gumroad

50K Day-One Users With Zero Marketing Spend

Sahil Lavingia grew up in Singapore, moved to LA at 17, and landed a job at Pinterest when the company had just four people. A year later, he left to solve a problem he had personally experienced: selling a digital file to a small audience was painfully difficult, even for someone who could design and code. So he built Gumroad in a weekend. He posted it on Hacker News, wrote a blog post, and tweeted about it. Around 50,000 people saw it on day one. What made Gumroad different was its product-led growth loop. Every time a creator sold something through the platform, the buyer experienced Gumroad firsthand. Many of those buyers were creators themselves who could use the same tool. Growth was built directly into the transaction. Sahil and his team never spent significant resources on acquisition. Instead, Sahil raised a $1 million seed round, left Pinterest, and focused entirely on building the product. A few years later, VCs came to him with term sheets, and he closed a $7 million Series A. The product-led growth engine kept working while the team focused on abstracting away complexity for creators - moving from raw file uploads to full content experiences for books, music, and film. Sahil also shares what he learned about leadership as a 22-year-old first-time CEO, why product-led growth let him focus on the product instead of sales, and how communicating the reasoning behind decisions became his most important leadership skill.