Big tech is transforming every aspect of our world. But how, and at what cost? This season of Land of the Giants – The Disney Dilemma – focuses on Disney’s ability to weather the ups and downs of the business cycle and changing tastes and explores what has kept it successful for over 100 years. The entertainment giant has leveraged nostalgia and its intellectual property to build a beloved brand, but after an acquisition spree that included Marvel, Lucasfilm, and 20th Century Fox, can it sus ...
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1 Shuai Wang’s Journey from China to Charleston 38:30
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LikedChef Shuai Wang was the runner-up on the 22nd season of Bravo’s Top Chef and is the force behind two standout restaurants in Charleston, South Carolina—Jackrabbit Filly and King BBQ—where he brings together the flavors of his childhood in Beijing and the spirit of the South in some pretty unforgettable ways. He grew up just a short walk from Tiananmen Square, in a tiny home with no electricity or running water, where his grandmother often cooked over charcoal. Later, in Queens, New York, his mom taught herself to cook—her first dishes were a little salty, but they were always made with love. And somewhere along the way, Shuai learned that cooking wasn’t just about food—it was about taking care of people. After years working in New York kitchens, he made his way to Charleston and started building something that feels entirely his own. Today, we’re talking about how all those experiences come together on the plate, the family stories behind his cooking, and what it’s been like to share that journey on national TV. Learn more about your ad choices. Visit podcastchoices.com/adchoices…
#127: Scaling SaaS with Efficient Growth and Practical Funding - Bryan Forrester
Manage episode 461568789 series 3408432
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Bryan Forrester is CEO of Boostlingo, a leading on-demand platform for language live interpretation services that is growing quickly and can become a very large company.
Boostlingo now has 160 employees and over 17,000 language interpreters who use their software to manage jobs, coordinate schedules, deliver interpreting services, and get paid.
Bryan raised some practical funds from angels to start the company in 2016. The company grew 50% or more every year since then. In 2021, Boostlingo raised a growth equity round of funding from Mainsail Partners to provide capital for efficient growth and buy out some early investors. Boostlingo has since made several small acquisitions.
Quote from Bryan Forrester, CEO and co-founder of Boostlingo
"Our customers love our software, and our NPS is very high. So when we have customers who love our software, we have high retention and low churn, and our customer costs are really good. When all of that is combined, why would you slow down the growth?
"Why would you take your foot off the gas pedal and be very profitable? And we raised a growth equity investment from Mainsail and started spending more on efficient marketing. And it worked. It worked.
"What would have happened if we didn't take that small investment with our growth equity partner? We could still have had a positive outcome. We may have already sold the business. But we wouldn't have grown as big as we have become in this very big market."
Links Podcast Sponsor - Cypress Growth CapitalThis week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. Message Cliff Sentell at Cypress to have an open discussion about your options.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
151 episodes
ShareManage episode 461568789 series 3408432
Content provided by Greg Head. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Greg Head or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://ppacc.player.fm/legal.
Bryan Forrester is CEO of Boostlingo, a leading on-demand platform for language live interpretation services that is growing quickly and can become a very large company.
Boostlingo now has 160 employees and over 17,000 language interpreters who use their software to manage jobs, coordinate schedules, deliver interpreting services, and get paid.
Bryan raised some practical funds from angels to start the company in 2016. The company grew 50% or more every year since then. In 2021, Boostlingo raised a growth equity round of funding from Mainsail Partners to provide capital for efficient growth and buy out some early investors. Boostlingo has since made several small acquisitions.
Quote from Bryan Forrester, CEO and co-founder of Boostlingo
"Our customers love our software, and our NPS is very high. So when we have customers who love our software, we have high retention and low churn, and our customer costs are really good. When all of that is combined, why would you slow down the growth?
"Why would you take your foot off the gas pedal and be very profitable? And we raised a growth equity investment from Mainsail and started spending more on efficient marketing. And it worked. It worked.
"What would have happened if we didn't take that small investment with our growth equity partner? We could still have had a positive outcome. We may have already sold the business. But we wouldn't have grown as big as we have become in this very big market."
Links Podcast Sponsor - Cypress Growth CapitalThis week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. Message Cliff Sentell at Cypress to have an open discussion about your options.
The Practical Founders Podcast
Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.
Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.
151 episodes
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1 #152: Practical SaaS CEO Stays On After 100% Cash Sale - Tracy Larson 1:04:10
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Play Later Play Later Lists Like LikedTracy Larson is President and CEO of WeSuite, a vertical sales automation platform designed for larger integrators who sell complete security systems for commercial and residential real estate. Tracy and the cofounders were in the security systems business before launching a sales software company for this market in 2008. WeSuite is now a comprehensive solution that addresses the complex industry requirements for lead tracking, quoting, proposal management, contracting, commissions, and pipeline management. Hundreds of integrators in the US use WeSuite for their end-to-end quote-to-contract process. WeSuite grew profitably to nearly $5 million in revenue in 2024, when the founders sold 100% of the company to Valsoft, a buy-and-hold acquirer of practical software companies. Tracy remains the CEO of the company, which operates independently in the Valsoft holding company. Quote from Tracy Larson, CEO and president of WeSuite “For founders in SaaS, especially women founders, you need to find the right people to become your personal board of advisors. You don't need money to pay them. Just pick five people who you've known over the years to help you. Ask them, Would you do this for me and be a sounding board once a month? I'd like to get your perspective on topics like these for 30 minutes. It’s not a formal board, it’s just advice and perspective. “Establishing a personal board of advisors is a great idea. They can be women or men. And you can switch it up every year or so. Don’t worry about what you don't know. We all have things we don't know.” Links Tracy Larson on LinkedIn WeSuite on LinkedIn WeSuite website Valsoft website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
1 #151: Facial Recognition SaaS for Casinos to Almost $10M in Revenue – Henry Valentino 1:02:52
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Play Later Play Later Lists Like LikedHenry Valentino is the founder and CEO of EConnect , a leading provider of facial recognition software for casinos and stadiums, ensuring venue security and compliance. He founded EConnect in 2009 and pivoted several times before focusing on a security platform utilizing AI for casinos during the COVID-19 pandemic. The Econnect platform offers facial recognition surveillance software that integrates with special cameras at venue entrances to identify known security risks and ensure compliance. Security teams get immediate identification of “known bad guys” in large venues. Econnect is approaching $10 million in revenue with hundreds of customers as a profitable business, with no outside equity funding. EConnect secured a total of $2 million in venture debt in 2019 and 2020, repaid it, and is now a growing and profitable company. Quote from Henry Valentino, CEO and founder of EConnect “Make sure you know your financial numbers yourself as the CEO. It's great to lean on accounting or finance leaders, but if you don't know them yourself, that's a big hindrance to success. “Cash is what it comes down to. If the bank account doesn't have enough cash, they're only calling one person to get that resolved and that's you. If you get into trouble, you'll be trying to cut costs, which is not a way to grow a SaaS business. “To continue growing, you need to increase your spending and capacity to take on new customers. How much does it cost to keep these doors open every month? How much cash are we going to bring in? What do we need to billl to put us in a profit position every month?” Links Henry Valentino on LinkedIn EConnect on LinkedIn EConnect website Costella Kirsch The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
1 #150: Grew an Unsexy Small Software Biz Into a SaaS Powerhouse - Josh Turley 1:16:36
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Play Later Play Later Lists Like LikedJosh Turley is CEO of RTA Fleet Management , a fleet management software company that his grandfather started in the 1980’s and ran as a small family business for decades. Then Josh’s father ran the business until 2015, never growing this slow, old-school business past $2 million in revenues. Josh had worked in the business before, but in 2016, Josh bought the business, to over as CEO and slowly began to make improvements—and mistakes—as they started to grow. Josh had an ambition to grow the company and learn how to be a real CEO. They started retooling their code to build modern cloud software, investing heavily for many years. They transformed their leadership, staff, business model, pricing, marketing, tech stack, and culture as they grew faster. They also focused on state and local government fleets as they grew. The bootstrapped company grew steadily, with 75 employees and a $15 million annual recurring revenue (ARR) run rate in 2024, supported by some debt. In 2025, Josh closed a $30 million investment round from Susquehanna Growth Equity, a practical growth equity investor that invests in steady SaaS businesses. Josh is a long-time member of my Practical Founders CEO Peer Groups . He is an avid learner, attending conferences, reading books, hiring consultants, and continually seeking new knowledge. In this episode, Josh also talks about: How difficult it was to transform an old business into a new one Why their Purpose, Values, and Mission drive successful hiring Why he chose to take on growth equity investors and de-risk with secondary investment Quote from Josh Turley, CEO of RTA “Every problem is a leadership problem. The biggest challenge in building a SaaS business is always the people—making sure you get the right people on the bus in the right seats. We’re at 90 people now, and there's no way I can manage 90 people myself. As the CEO, it all starts with you, then your leaders. “Most problems I see are because we got the wrong person in the wrong seat. You can't outrun that, regardless of how good the product is or how strong your financial model is. It will always catch up to you eventually, and that causes more problems than anything. “When you get a leadership team to be 100% aligned with one another, it doesn't matter what the market's doing. It doesn't matter what the product is doing. It will figure itself out. It's a forcing function to get that alignment, and then you just can't be stopped at that point.” Links Josh Turley on LinkedIn RTA on LinkedIn RTA website Susquehanna Growth Equity website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
1 #149: How Partner-Led Sales Built A $7M Bootstrap SaaS Business - Sameer Narkar 1:03:58
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Play Later Play Later Lists Like LikedSameer Narkar is the founder and CEO of Konnect Insights , a global SaaS company based in Mumbai that provides an omnichannel customer experience platform to consumer brands in 100 countries. Sameer created Konnect Insights in 2015 to help customer service teams respond to customers who mention their brands on social media. The product and company have expanded from a slow start working through marketing agencies in India to now distributing through ISV partners in all major global regions. The Konnect Insights product includes social listening, ticketing, reputation monitoring, and social media analytics. They have grown to 140 employees, hundreds of customers, and $7 million ARR--without any outside funding. In this episode, Sameer talks about: Selling through agency and ISV partners to grow efficiently Competing with large, well-funded software companies How he thinks about how AI can help them compete Why he hasn’t sold the company or raised outside funding Quote from Sameer Narkar, founder and CEO of Konnect Insights “When you start a software company, you have all odds against you. You don't have enough money. There's no reason why customers would trust you against the established products. There is a 99% chance that you'll fail. “But if you're really passionate about what you're building, then don't look too far ahead. Try to achieve your smaller goals or get from zero to one. So just build something and get some early customers. We figured out a way for agencies to be interested in selling our solution to bring it to market. “Then meet directly with your end customers. It's very easy for tech founders to sit in the office and build a product the way they think. That doesn’t work. Many founders think that if they take a half-baked product, they won't get another chance. But that's not the case. You need to build relationships to help you improve and grow..” Links Sameer Narkar on LinkedIn Konnect Insights on LinkedIn Konnect Insights website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
1 #148: These Bootstrappers Sold Modern Digital LeadGen to Conservative German Businesses - Chris Erler 55:44
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Play Later Play Later Lists Like LikedChris Erler was co-founder and COO of ComX, a sales pipeline generation for mid-market B2B companies in Germany and Europe. Chris and two other founders started the company in 2018 to conduct turnkey modern digital marketing and lead generation solutions for traditional German companies. As a tech-enabled service that combines technology, data, and people-powered solutions, ComX delivers proven results through subscription and outcome-based pricing. They grew quickly to approximately $20 million in revenue in four years before being acquired by the private equity firm FLEX Capital. In this episode, Chris talks about: Growing a team of 70 employees in South Africa Starting in Germany with mid-market companies The challenges of debt financing of private equity buyouts Quote from Chris Erler, cofounder of ComX “99% of the time, I ask the founder, Why are you raising money from investors that early? I'm very pushy on that one because I know the freedom that you can create when building a bootstrapped business. “For me, raising money from investors and giving away shares very early means you’re not focusing on customers, but rather focusing on collecting capital to build the product without having it validated too early. I just share our bootstrapped story with ComX which I believe works well. “That's why I'm a big fan of your podcasts. There's a huge education needed, especially in Europe. People need to be educated on how to found properly. Of course, it can go well, but the chances that something f***’s up are much higher. And then young people are in a very bad situation.” Links Chris Erler on LinkedIn ComX on LinkedIn ComX website FLEX Capital website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
1 #147: How a Philadelphia Insurance Agent Built the Uber of Surety Bonds - Aaron Steffey 1:04:44
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Play Later Play Later Lists Like LikedAaron Steffey is the co-founder and co-CEO of Propeller , an online platform that enables insurance agents and brokers to issue surety bonds instantly — without the lengthy paperwork or back-and-forth typically involved in bonding. Aaron was an insurance agent, and his co-founder cousin, Chris, was a surety bond underwriter before 2019, when they set out to revolutionize the way surety bonds are bought and sold. They initially bootstrapped with a software development partner who accepted equity instead of fees. Their first version drastically simplified the process of buying and selling surety bonds in the digital world, allowing them to grow quickly. They raised $7 million in SAFE notes from strategic partners to accelerate growth in 2021 and grow to nearly $20 million in revenue. They sold 100% of the company to Arch Capital in a strategic acquisition in early 2024. In this episode, Aaron also talks about: How this sleepy, paper-based market changed quickly in COVID Why they raised growth funding from strategic investors and not VCs Why they sold the company and are still leading the business after the sale Quote from Aaron Steffey, co-founder and co-CEO of Propeller “My biggest advice for startup founders is simply just that endurance wins. It’s the whole thing of getting back up after you're knocked down, like everyone says. I had to live that so many times. So many No's when it came to our first carrier pulling out. No, I don't want to invest. No, I don't want to use your surety product. “There were so many times when I wanted to give up. And the same with my cousin. Had we not founded the company together, I don't know that we would have continued because there were probably times when I would have given up. “As long as both of us weren't on the floor, one of us would just pick the other up when the other person usually was more sane, and we dragged each other along. “A successful founder needs to have a pretty high pain tolerance and endurance to succeed. You just have to keep pushing forward. It just sounds so cliche, but that’s what it was for us.” Links Aaron Steffey on LinkedIn Propeller on LinkedIn Propeller website Arch Capital website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
1 #146: This European SaaS Bootstrapper Raised $22M in Growth Equity Without Losing Control - Roy van den Broek 1:00:46
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Play Later Play Later Lists Like LikedRoy van den Broek is the founder and CEO of Rentman , a rental business management software platform for event and media production companies. Roy built software for his event equipment rental business in the Netherlands. He had over 100 software customers in Europe before selling his rental equipment company in 2015 to focus on growing his Rentman SaaS company. Rentman grew slowly and profitably as word of mouth spread in the industry and their product evolved. In 2024, after growing to nearly 100 employees and 200,000 users across 100 countries, Roy raised a $22 million growth equity round from Expedition Capital to derisk the founder's investment and add growth capital to continue expanding. In this episode, Roy discusses how they managed the painful growth stages as they expanded from one employee to 80 global employees, building a multi-lingual product and business, and why he chose to raise a significant growth equity investment. Quote from Roy van den Broek, founder and CEO of Rentman “We had a lot of interest in investing in Rentman after COVID, so we ran a quick process. We ended up with 3 term sheets. You have multiple ways to look at these term sheets. You can look at the numbers and the valuation, which is a big part. “But what's often overlooked is the other terms. The other terms are as important as the valuation because they really determine the way you work together. I think these terms might even be important or more important than the valuation. You got to understand their game and really figure out if you could get some alignment. “In essence, you are negotiating the amount of autonomy that you have as a founder. That's basically what we prioritized. Like the board seats and who makes certain decisions, what are the decisions that require a majority vote? And I think we were able to get 100% autonomy on our side.“ Links Roy van den Broek on LinkedIn Rentman on LinkedIn Rentman website Expedition Growth Capital website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
1 #145: Making Big Bold Bets with Patient Execution as a Bootstrapped Founder - Gopal Krishnamurthy 59:50
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Play Later Play Later Lists Like LikedGopal Krishnamurthy is the founder and CEO of Lumel , which has a suite of products focused on enterprise performance management (EPM). Their apps allow users to plan, report, and analyze data using the modern native app framework vs. traditional SaaS on top of modern cloud data platforms such as Microsoft Fabric, Snowflake, Databricks, and others. Lumel’s products provide a full stack of integrated Planning, BI & data apps on the customers' data platforms. He grew his enterprise services company, Visual BI, to over 200 employees and sold that company to Atos in 2021, as he described in his first Practical Founders podcast interview in 2023. Gopal self-funded Lumel with a VC-sized investment and has grown it to over 300 employees in four years. Lumel is already at a revenue run rate of over $12M ARR and is growing fast. Lumel is building its apps using modern cloud data platforms, not siloed SaaS databases, allowing it to manage real-time data across applications. This bold new vision and architecture for enterprise software apps align with modern data approaches supporting AI, creating a billion-dollar opportunity for Lumel in the future. In this episode, Gopal also discusses: The challenge of transitioning from custom services to a no-touch product-led approach selling to enterprises Why VCs wouldn’t understand their technology bet and why their patience is paying off What it’s like to grow a fast-growth and innovative technology company as a bootstrapper Quote from Gopal Krishnamurthy, founder and CEO of Lumel “The main thing is it’s a big market. It’s not like we are just trying to get our first $10 million revenue. We have done that with Lumel already. We are looking at how we can get to a billion-dollar ARR business. That’s the big, bold vision. We have invested tens of millions already, and we are almost profitable. “We think we can absolutely create a billion-dollar business based on our customer feedback and traction from 3,000 customers. So, it’s not a question of product market fit. We worked with hundreds of our enterprise customers and perfected our data app products. “The other thing is that our products can work for smaller and medium-sized businesses because of our architecture and approach. It's completely horizontal: it works for all industries and all customers of all sizes.” Links Gopal Krishnamurthy on LinkedIn Lumel on LinkedIn Lumel website Power BI website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
1 #144: From Founder-Led Sales to Scalable Go-To-Market in Vertical SaaS - Phil Stern 58:20
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Play Later Play Later Lists Like LikedPhil Stern is the operating principal of Mainsail Partners , a growth equity firm that invests in bootstrapped vertical SaaS companies. Mainsail offers deep operating support to the leaders in their portfolio companies to help them grow more efficiently. Phil leads the GTM operations team, helping their founders scale sales, marketing, and success teams. Phil was an experienced SaaS sales leader at several companies before joining Mainsail to focus on helping their portfolio companies scale up to $30M ARR or more. Phil’s team helps founders solve challenging problems with sales leadership, rev ops technology, compensation, marketing analysis and planning, and more with deep operational insights customized for each company. In this episode, Phil discusses these important topics. The five keys to hiring your first head of sales to graduate from founder-led sales to a scalable sales team How Mainsail specialists partner with founders and their leaders to help them solve their most important GTM problems quickly How Phil helps with due diligence on potential investments to assess the upsides and opportunities for revenue growth Why Mainsail is focused on vertical SaaS companies with founders who are experts in their domains Quote from Phil Stern, Operating Principal at Mainsail Partners “Hiring a first head of sales is typically one of the first roles we're going to hire. This sales leader needs to be willing to sell the product. You're not coming in at $5 million of ARR to be an armchair VP. You own part of the quota, you're going to cover for a rep at a trade show or on maternity leave, whatever it takes. “You have to be willing to sell. So if you come in just to strategize and move chess pieces around, it's just not the job for you. “If you don’t sell, you won't get close enough to the customer. For these customers in vertical end markets, you need to get close to them, learn from them, understand them, and speak to them. “It's really back to a bootstrapper mentality. The CEO has been doing absolutely everything up and down the business. I'm asking a sales leader to do everything up and down the go-to-market.” Links Phil Stern on LinkedIn Mainsail Partners on LinkedIn Mainsail Partners website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
1 #143: From Professional Services to a $30M SaaS Business with a PE Acquisition - Sean Hoban 1:04:53
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Play Later Play Later Lists Like LikedSean Hoban was co-founder and former CEO of Kimble Applications, a leading professional services automation (PSA) software for organizations to manage their professional services business's entire operational and financial lifecycle. Sean and his co-founders had already started, grown, and sold a pro services organization before creating a PSA product and building a SaaS business. With a little funding from the founders and a few angel investors, Kimble started efficiently and grew steadily, eventually raising a practical minority funding round from private equity investors Accel-KKR in 2018. The company grew to $30M ARR before selling most of the company to Accel-KKR in 2021, which merged two PSA companies to create Kontata . In this episode, Sean discusses some of their deepest strategic opportunities: Learning to grow a SaaS business versus a professional services organization Building on the Salesforce platform and working in that ecosystem Starting in the UK and expanding to Germany and the US Quote from Sean Hoban, former CEO and co-founder of Kimble Applications “One of the most powerful ways I learned as a CEO is to find and talk to other founders in London who were in a similar situation. We would meet for beers, share ideas, and chat on WhatsApp. “If you have a specific problem, it was valuable to talk to other founders in the same growth stage. And these were founders, not hired CEOs. “It's a lonely job as a CEO. And being able to talk to somebody else who is in a similar position can be cathartic and very helpful.” Links Sean Hoban on LinkedIn Kantata on LinkedIn Kantata SX (formerly Kimble Applications) website Accel-KKR website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
1 #142: Why This 3x SaaS Founder Couldn't Stay Retired to Launch His New Al Startup - Josh LaSov 58:37
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Play Later Play Later Lists Like LikedJosh LaSov is the founder and former CEO of Satori Reporting, an advanced reporting and business intelligence (BI) solution for mid-market businesses that use NetSuite financial software. Satori provided pre-built reports and dashboards, a tailored data warehouse, and detailed data models that leveraged the popular Power BI software. Josh launched Satori, his second NetSuite solution, in 2019 and grew quickly in the NetSuite ecosystem, with a savvy team and no outside funding. Satori was sold it to private equity buyer Insight Partners in 2022 and combined with another NetSuite provider, Zone & Co. In this episode, Josh talks about the benefits and challenges of building add-on solutions in the NetSuite ecosystem, their ROI of non-dilutive funding and strategic angel investors, selling two companies then getting bored and restless, and starting his third company, Cauzzy.ai to provide AI-powered automated financial analysis and insights. Quote from Josh LaSov, founder of Satori Reports and Cauzzy.ai “When you have a good exit, you can assume the lifestyle that you desire to live, you can slow down. So from 2022 until starting Cauzzy.ai in 2024, I did that, I worked out every day. I listened to more podcasts than any human should listen to. I educated myself, read every newspaper and news site. I took time for myself “What I found was...it wasn't fulfilling. I needed more. I didn't want to be on the sidelines. I felt myself getting slower, like I was retiree. I appreciated the journey more than the destination. But there's a balance and I could achieve that balance. “I needed to do something, but I didn't want to just jump into something just to do it. I was to be patient until I found something that I was passionate about and that's realizable. I thought, I can do this again, I want to do this again. Let's take our time and focus a bit more on balance this time, but let's get back in the game.” Links Josh LaSov on LinkedIn Zone Reporting (formerly Satori Reporting) on LinkedIn Zone Reporting (formerly Satori Reporting) Cauzzy.ai website NetSuite website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
1 #141: Inside Acquire.com's Process for Selling Sub-$5M SaaS Companies - Andrew Gazdecki 55:39
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Play Later Play Later Lists Like LikedAndrew Gazdecki is the founder and CEO of Acquire.com , a marketplace of buyers and sellers of smaller, profitable SaaS products with revenues between $100,000 and $5,000,000. Andrew sold his own software company and learned how little support and information was available to sell a software product for under $5-10 million in deal size. Acquire.com has helped over 2000 entrepreneurs sell their software products for a combined value of more than $500 million. Acquire offers additional support to help founders package, promote, negotiate, and close their transactions. Potential buyers are vetted for financial viability and identity confirmation before getting confidential details for any deal. In this episode, Andrew describes their typical seller and buyer profiles, the typical process for a founder to sell a small and profitable SaaS company, typical multiples of profit that financial buyers offer, and founder transition periods. Quote from Andrew Gazdecki, founder and CEO of Acquire.com "There are three buckets of active buyers on Acquire.com. The first is below $100,000 net profit. That's going to be an individual buyer looking for something with maybe a little bit of product market fit. They want to take the product, grow it a little bit, see what they can do from there. They're buying a very, very early startup. So some buyers will actually start small and then work their way up. "From $100,000 to $1 million in net profit in our middle range, the buyer will a blend of "micro PE firms" and holding companies that want to get their hands on a business where there's a lot more going on. And then a $1 million in profit and above is going to be for the more traditional private equity or strategic buyers." Links Andrew Gazdecki on LinkedIn Andrew Gazdecki on Twitter Acquire.com on LinkedIn Acquire.com website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
1 #140: The Anti-Silicon Valley Playbook: How Genius Monkey Built a $100M Ad Tech Business on Their Own Terms - Seth Hassell and Clint Ethington 1:04:34
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Play Later Play Later Lists Like LikedSeth Hassell and Clint Ethington are the co-founders of Genius Monkey, a programmatic ad tech platform with proven targeting, tracking, and attribution for optimized results. Seth and Clint were childhood friends who worked on many business ventures before launching Genius Monkey in 2009, leveraging their experience in digital ad technologies. Genius Monkey grew steadily as a bootstrapped company, with the founders and team working hard for years to improve their platform, prove results to clients, recruit agencies, and grow their team. Most ad tech peers took VC funding and are no longer around, but Genius Monkey is still growing and getting more profitable every year. In this episode, Seth and Clint talk about their unusual long-time partnership, the power of profits, competing with giants, building a strong company culture, and leveraging non-dilutive funding to grow faster. Quote from Seth Hassell and Clint Ethington, co-founders of Genius Monkey "Don't be afraid to fail with the smaller stuff. A lot of times, people don't take the chance of seeing, "What if we do it this way?" What happens? And all those little things that could become something big, they never pursue because they're comfortable with where they're at." "Fail fast. Try stuff out. If you see it's not working, shelf it and go to the next thing. Move on until you find that one that's doing better than where you're at right now. Then, I will put the determination and the motivation behind it to see it through. Clint and I tried through lots of things that just didn't work out." "If it wasn't working, we were okay. We wouldn't say, "It's all over, close the doors." It wasn't like that. It was like, "Okay, we know that doesn't work. What's our next thing we're trying?" And we always had different ideas in the background." Links Genius Monkey on LinkedIn Genius Monkey website Cypress Growth Capital website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
1 #139: Bootstrapped Founder is Getting Ready for the AI Wave at $20M ARR - Shalin Jain 1:07:35
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Play Later Play Later Lists Like LikedShalin Jain is the founder and CEO of HappyFox, a successful bootstrapped company that provides modern help desk management software for customer service, support, and IT management organizations. Shalin and his small team in India built many successful products from 2000-2010, then focused on HappyFox and moved to the US in 2011. HappyFox is a mid-market product that sells across industries and departments with an efficient product-led growth (PLG) approach. The product has matured with successful add-on products for live chat, AI support, business intelligence, and workflows. The company has over 2200 customers, 110 employees, and now $20 million in revenue. Shalin plans to keep growing and leverage modern AI technology to become a much bigger company based on the disciplined product culture they have created. Quote from Shalin Jain, founder and CEO of HappyFox “I think software and its pricing need to be deflationary, just like hardware, where memory prices, hardware prices, and server prices have all been deflationary. But we are now going through a phase where software is actually getting more and more expensive. “With the advent of AI and automation, software will become cheaper and more usage-driven. So, the best survivors in that phase would be the efficiently run companies that have not bloated themselves by charging more today to have more employees and spend more on ads. “I believe software needs to get cheaper because it's getting cheaper to run software every day; it's getting cheaper to outsource to AI and build stuff with the help of AI as well. So software cost should not go up; it should go down.” Links Shalin Jain on LinkedIn HappyFox on LinkedIn HappyFox website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
1 #138: Achieved Strategic Acquisition Just 2 Years After Launch - Brian Kesselman 1:00:15
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Play Later Play Later Lists Like LikedBrian Kesselman is cofounder and now CRO of Skematic , a compliance management and workflow software for financial services firms. Brian was a lawyer for major financial services companies who helped manage internal compliance in this highly regulated industry. He took a job selling compliance software and broke sales records before starting Skematic with a coworker and launching in September 2022. Skematic grew quickly by solving an acute problem for lawyers and compliance execs just like him in his industry. The company became profitable quickly as Brian focused on outbound selling with cold calls and savvy demos to busy compliance executives. They grew fast, were profitable in just over a year, and attracted attention from potential acquirers. In June 2024, Financial Recovery Technologies, a fintech legal software company, acquired Skematic for an undisclosed amount, including some cash and incentives. Brian and his cofounder still run Skematic and enjoy being part of a bigger software company owned by a private family office that is highly aligned with their culture and values. Quote from Brian Kesselman, cofounder and CRO of Skematic "My co-founder Charles and I had worked at a number of PE-backed software companies. And we had our own opinions about what it's like to work at a PE-backed company." "The family office structure is very different from a private equity firm across the board. They're looking typically to build profitable cash-producing assets. And so that enables our team to think long-term, which benefits not only the founders and the people that are still participating in the upside of the business." "That also means that the clients will benefit because you are going to do things that will benefit the clients every step of the way, one year, two years, five years, 10 years. And that was paramount to us, given that we've grown up in this very niche industry and our reputations to us are pretty much everything we have." Links Brian Kesselman on LinkedIn Skematic on LinkedIn Skematic website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
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1 #137: Her Amazing Story of 0-$30M ARR with No Outside Funding - Rebecca Shostak 1:04:57
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Play Later Play Later Lists Like LikedRebecca Shostak is co-founder and chief brand officer of Flodesk , the popular email marketing software for small businesses that care about beautiful branded emails. After prototyping the product and validating the problem, they launched in 2019 with a viral explosion that still powers their bootstrapped growth. Six years later, Flodesk has over $30M in annual recurring revenues with 75 employees and over 100,000 paid customers. They have been profitable since the second week after launch, driven by great product design, the email footer “viral loop,” and referrals from customers and influencers. In this episode, Rebecca shares her insights on product design, their unlimited pricing model, working with her co-founder/CEO, Martha Bitar, why they haven’t taken outside funding, and where AI is showing usefulness in their products. Quote from Rebecca Shostack, co-founder of Flodesk “The reason you hire is never to solve a problem. You need to be sharp and figure out how to solve the problem on your own. Then, you hire people once you've proven something. “When you want to hire someone to run your paid ads, for example, you first need to figure out the basics. Then, you can hire someone to come in to own that so they can scale that operation. “But it doesn't work to hire someone to come in and figure out something that you can't figure out yourself. How can you hire someone to manage something you don't understand?” Links Rebecca Shostak on LinkedIn Flodesk on LinkedIn Flodesk website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
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1 #136: Practical Founder Has Big Exit and Un-Retires to Build 2nd SaaS Success - Brian Dosal 1:11:26
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Play Later Play Later Lists Like LikedBrian Dosal was the founder and CEO of BrightGauge, a software company he bootstrapped and grew to almost $10M ARR with his brother before successfully selling the company in 2019. BrightGauge was a business analytics and dashboard for key metrics for the Managed Service Provider (MSP) industry. After his intense 9-year journey at BrightGauge, Brian “retired” to spend more time with his growing family. He enjoyed his free time but eventually returned to the software startup game with his second company, Strety. Strety is a fast-growing SaaS business with a popular app for small businesses using the EOS® approach to manage their businesses. It has 10 employees, hundreds of customers and partners, and no outside funding. Brian brought back some of his previous team to build another sustainable and valuable software company. Links Brian Dosal on LinkedIn BrightGauge website Strety on LinkedIn Strety website Entrepreneurial Operating System (EOS) website Traction book by Gino Wickman Anything You Want book by Derek Sivers The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.…
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1 #135: Vertical SaaS Investor Shares Proven Paths to Scale Up Big – Dave Yuan 55:49
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Play Later Play Later Lists Like LikedDave Yuan is the founder of Tidemark , an active growth equity investor focusing on vertical SaaS companies with outsized advantages that can become “control points” in their markets and grow very big. Dave and Tidemark have invested in successful companies like Toast, ServiceTitan, Karbon and Dutchie. In this episode, Dave shares some of the most useful strategic growth frameworks for vertical SaaS companies to grow through winning market share, expanding with additional products, and even extending through an industry ecosystem serving new markets. We also talk about the impact of AI on established vertical SaaS players and how it’s both an opportunity and a thre Tidemark supports the global community of practical vertical SaaS founders by publishing their strategic growth frameworks , their annual Vertical SaaS Benchmarketing Report, and they host the annual Vertical SaaS Collective Live conference for founders. Quote from Dave Yuan, founder at Tidemark “Vertical SaaS founders should not be asleep with AI. You can wave it off, view it as a toy, and say that no one’s going to trust that outcome or use it. That may have been the case, but things are changing really quickly. “Lots of smart people are making it better every month, and you have a massive opportunity to improve it with your data and workflow. “Jump into it to control your destiny. Don’t get caught sleeping without AI in your product in a useful way.” Links Dave Yuan on LinkedIn Tidemark on LinkedIn Tidemark website Tidemark Vertical SaaS Knowledge Project VSaaS Collective Live 2025 conference Vertical SaaS Benchmark Report 2024 The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.…
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1 #134: When It’s Time to Close: Helping Founders Shut Down Right – Dori Yona 44:27
44:27 Play Later Play Later Lists Like Liked44:27
Play Later Play Later Lists Like LikedDori Yona is co-founder and CEO of SimpleClosure, a technology- and people-powered company that helps founders wind down and dissolve a startup or business that is no longer viable. Shutting down a business can be complicated, costly, and risky for founders. SimpleClosure manages the unique processes with automation and expert support. SimpleClosure has helped tech startup founders wind down over 500 startups, businesses that closed or have gone through a sale of assets. It manages the important steps of a winddown, including legal, regulatory, employees, investors, intellectual property, customers, data, and more. In this episode, Dori shares the key considerations for SaaS founders who have run out of VC funding or need to shut down their companies for other reasons. Quote from Dori Yona, CEO of SimpleClosure “The biggest thing for software startup founders and CEOs is to move fast. Your time is your biggest resource in life as an entrepreneur, whether you’re venture-backed or bootstrapping. You’re spending your time, you’re spending your energy, you’re spending the best years of your career. “So move fast, learn fast, test fast, iterate quickly, grow fast, fail fast. Ultimately, when you’re building your own business, you’re sacrificing an easy, convenient, cushy job anywhere else to take this risk. “The faster you can grow, learn, build, and fail, the better. It’s ultimately to your advantage to make the most of your time. Our time is our most expensive resource.” Links Dori Yona on LinkedIn SimpleClosure on LinkedIn SimpleClosure website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.…
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1 #133: Bootstrapper Sells School Fundraising Platform to PE Investors - Howard Gottlieb 58:47
58:47 Play Later Play Later Lists Like Liked58:47
Play Later Play Later Lists Like LikedHoward Gottlieb started Read-A-Thon in 2012 as a reading-based fundraising platform that helped students raise money while boosting education. Their easy platform and simple fundraising approach created amazing results. The Read-a-Thon business grew steadily and profitably without any outside funding. Read-A-Thon helped over 4000 schools and students raise over $30 million in donations. Their platform has tracked over 30 billion reading minutes by students who have used it to earn donations. Read-A-Thon was successfully acquired by private equity investors in early 2023 for an undisclosed amount. The business has continued to grow and expand with a new CEO and key executives, with Howard on the board as an advisor and now a minority investor in the company. Quote from Howard Gottlieb, founder of Read-A-Thon “I have been very blessed and very lucky in my journey with the success of Read-A-Thon. Everyone should realize that and have some humility. “If you succeed at the game, you can be the smartest guy or the smartest woman with the most brilliant idea, but it still will take 50% or more luck for everything to align correctly to succeed. Just realize that. It takes a lot of good fortune. “At Read-A-Thon, our lucky moment was COVID because online fundraising was only in its infancy. When COVID hit and schools were out, Read-A-Thon was almost the only viable option. Our growth went from 40% a year to 100%, then 150% a year. So that was luck after all these years.” Links Howard Gottlieb on LinkedIn Read-A-Thon on LinkedIn Read-A-Thon website The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.…
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1 #132: Bootstrapper Serving Private Equity Firms Acquired by PE-Backed Strategic – Richard Change 1:09:35
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Play Later Play Later Lists Like LikedRichard Change is co-founder and CEO of PFA Solutions , the provider of FirmView software. FirmView® is the leading carry and compensation management platform for private equity investors to manage their internal compensation from fees and carried interest. Richard was a senior architect for a large private equity firm when he discovered this complex problem that was being managed on spreadsheets. He left to start PFA Solutions and bootstrapped the development of FirmView with consulting revenue. From inception, through growth and ultimately acquisition, Richard never took any outside funding. FirmView adoption grew steadily, serving large private equity firms. PFA Solutions eventually grew to 34 employees before being acquired by Allvue Systems in 2024. Allvue is a private-equity-backed software company that serves the alternative investment industry. Quote from Richard Change, co-founder and CEO of PFA Solutions "Once you're in it, once you've decided to start a company, own it. No regrets. No one's going to save you. There's not a fairy godmother that will come and wave all your problems away. You have to own it. "There's no magic wand that will come and wave a wand and say, OK, all your problems are solved. And that magic wand in my mind wasn't outside capital; it wasn't VC funding. That wasn't magic because what do when the money runs out? "Is your product generating revenue? That's the real problem. If there's a problem to be solved and you have a great idea or solution, you can generate revenue from it. Prove to yourself and the world that this is viable and has product-market fit." Links PFA Solutions on LinkedIn PFA Solutions website Allvue Systems website Vista Equity Partners website Podcast Sponsor - Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital . For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. Message Cliff Sentell at Cypress to have an open discussion about your options. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.…
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1 #131: No-Code SaaS Platform Bootstrapped to 75,000 Customers – Rachit Khator 1:03:43
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Play Later Play Later Lists Like LikedRachit Khator is the founder and CEO of Stackby, a no-code spreadsheet and database app builder that allows business users to create powerful spreadsheet-like applications with data links, automations, and workflows. Rachit and his team of 34 employees live in Surat, India, north of Mumbai. Stackby started when Rachit was working for a corporate venture firm in Michigan, doing repetitive manual data imports and analysis in Excel. He hired a developer to build a better tool and started to sell Stackby to early customers. They followed customer feedback to build an inexpensive and easy-to-use app that competes well with VC-funded competitors like AirTable for specific use cases. This bootstrapped company has grown in 4 years to serve 75,000 free and paid business customers. Now they are profitable and growing at 15% per month, upselling free business users to paid plans. Rachit has big ambitions for Stackby to serve millions of customers–and be an example success story in the Surat software community. Links Rachit Khator on LinkedIn Stackby on LinkedIn Stackby website Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale , one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.…
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1 #130: Profitable Product-Led Growth to $30 Million Before Big Exit – Joe Hyrkin 1:07:58
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Play Later Play Later Lists Like LikedJoe Hyrkin is the former CEO of Issuu, a content publishing platform for interactive marketing content. Issuu allows you to easily publish printable and PDF materials in various formats to websites and social media. It’s a global product-led success story with millions of customers and a successful and sustainable business. Issuu was started by four Danish founders before the company was moved to Silicon Valley in 2013 when Joe was hired as the CEO. Joe ran the company for almost 12 years, growing it profitably most years to almost $30 million in revenue before it was sold in mid-2024 to Bending Spoons, an Italian holding company that is an active acquirer of software companies. Joe talks about working with their early venture capital investors with a practical and patient approach. In 2021, Issuu raised $20 million in debt to invest in marketing and address technology issues, which helped them grow faster before being acquired. Quote from Joe Hyrkin, former CEO of Issuu “ From 2016 to 2020, we ran Issuu profitably, with what I like to call a ‘pro-grow’ approach—profitable and growing. Then, we raised debt to grow faster to about $30 million in revenue. The final year before we sold, we got back to profitability. So we got to profitability twice. “By being profitable, you’re committing to your customers that you’re going to be around and that they will not have to go find some other solution. You’re communicating to your team that this company can be counted on. In 2024 and 2025, everybody wants profitability, unless you’re an AI company. “Not having a profitability plan actually creates a lot of risk. I’m not saying you always have to be profitable, but you always have to have a foundation to know how we get to profitability. It’s a different way of thinking.” Links Joe Hyrkin on LinkedIn Issuu on LinkedIn Issuu website Bending Spoons website Podcast Sponsor – Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital . For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. Message Cliff Sentell at Cypress to have an open discussion about your options. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.…
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1 #129: On Freedom and Ownership With Software Entrepreneur Brian Hamilton 1:06:34
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Play Later Play Later Lists Like LikedBrian Hamilton is one of America’s most successful entrepreneurs and a leading expert on entrepreneurship. Today, Hamilton serves as chairman of software company LiveSwitch . He is known for his pioneering work in fintech, his advocacy for small businesses, and his commitment to criminal justice reform. As the founder of Sageworks (now Abrigo), America’s first fintech company, Hamilton developed technology that translates complex financial data, empowering millions of small business owners. Sageworks struggled and grew slowly for 10 years before pivoting to serve local banks and credit unions with financial tools to assess the creditworthiness of their small business loans. The practical SaaS company grew steadily and very profitably to more than 400 employees when it was sold in 2018. Through Inmates to Entrepreneurs and the Brian Hamilton Foundation, he encourages entrepreneurship as a means to economic opportunity. Hamilton’s work has been showcased by major media outlets like CNBC and Good Morning America, and he starred in ABC’s Free Enterprise TV series, an award-winning show based on Inmates to Entrepreneurs. Quote from Brian Hamilton, founder and former CEO of Sageworks "Being the founder of a tech company is like this: You're in a tunnel, it's dark, you're on your hands and knees, you're going through that tunnel, you're groping your way through, keep moving forward. "I know it sounds like such a BS, but we've all been there. I'm telling you, that is the picture: you're in this huge sewer tunnel, it's dark. You just gotta keep moving. Just keep chipping away. You do that, and you will get momentum somehow. "It's like compound interest. You start with a dollar and how does it turn into $10? You build momentum a little at a time. I've got to listen every day. I'm knocking off making the product better. You develop the physical property of compound interest and things will get better." Links LiveSwitch website Brian Hamilton Foundation Podcast Sponsor - Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital . For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. Message Cliff Sentell at Cypress to have an open discussion about your options. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.…
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1 #128: Solving a Challenging SaaS Growth Puzzle - Scott Desgrosseilliers 1:04:33
1:04:33 Play Later Play Later Lists Like Liked1:04:33
Play Later Play Later Lists Like LikedScott Desgrosseilliers is the founder and CEO of Wicked Reports , a leading multi-touch marketing attribution software for SMBs who use paid online advertising. Scott is a data and analytics expert who saw the costly limitations of simple performance reports from popular ad platforms. Wicked Reports was started as a bootstrapped software company in 2016 to serve smaller companies that spend millions on digital ads and other marketing, including email, SEO, and digital events. Determining which marketing activities drive incremental revenue is a tricky puzzle to unravel, but the payback of those insights is huge. Scott raised a little angel funding and a little SaaS debt and is still going strong with 28 employees and is figuring out their growth and retention puzzle to accelerate growth. Quote from Scott Desgrosseilliers, founder and CEO of Wicked Reports "We had offers, and we could have raised VC funding early on, but then the growth rate we would have had to hit was too high, which didn't make sense for our business. "A competitor of ours took $20 million from a similar VC, and then they had to cut a third of their team. I'm not saying anything against them. They have a nice product and they seem like good guys. They hired a ton of people and didn't hit the growth number, so they had to whack a bunch of them. "Money isn't always the answer. I'm sure there are cases where it solved all sorts of problems, but most VCs want to invest when you already have growth and net revenue retention at 120% when the efficient growth problem's already solved!" Links Scott Desgrosseilliers on LinkedIn Wicked Reports on LinkedIn Wicked Reports website Podcast Sponsor - Full Scale This week’s podcast is sponsored by Full Scale , one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.…
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Practical Founders Podcast
1 #127: Scaling SaaS with Efficient Growth and Practical Funding - Bryan Forrester 1:11:52
1:11:52 Play Later Play Later Lists Like Liked1:11:52
Play Later Play Later Lists Like LikedBryan Forrester is CEO of Boostlingo, a leading on-demand platform for language live interpretation services that is growing quickly and can become a very large company. Boostlingo now has 160 employees and over 17,000 language interpreters who use their software to manage jobs, coordinate schedules, deliver interpreting services, and get paid. Bryan raised some practical funds from angels to start the company in 2016. The company grew 50% or more every year since then. In 2021, Boostlingo raised a growth equity round of funding from Mainsail Partners to provide capital for efficient growth and buy out some early investors. Boostlingo has since made several small acquisitions. Quote from Bryan Forrester, CEO and co-founder of Boostlingo "Our customers love our software, and our NPS is very high. So when we have customers who love our software, we have high retention and low churn, and our customer costs are really good. When all of that is combined, why would you slow down the growth? "Why would you take your foot off the gas pedal and be very profitable? And we raised a growth equity investment from Mainsail and started spending more on efficient marketing. And it worked. It worked. "What would have happened if we didn't take that small investment with our growth equity partner? We could still have had a positive outcome. We may have already sold the business. But we wouldn't have grown as big as we have become in this very big market." Links Bryan Forrester on LinkedIn Boostlingo on LinkedIn Boostlingo website Mainsail Partners website Podcast Sponsor - Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital . For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. Message Cliff Sentell at Cypress to have an open discussion about your options. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.…
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Practical Founders Podcast
1 #126: Jason Fried on 20 Years Bootstrapping BaseCamp at 37signals 57:57
57:57 Play Later Play Later Lists Like Liked57:57
Play Later Play Later Lists Like LikedJason Fried is the co-founder and CEO of 37signals, makers of the popular Basecamp project management software, which is still growing and very profitable after 20 years. He is going long and still having fun as an engaged CEO, building great products with great marketing that stands out. Jason has long advocated for software founders to avoid VC funding and build sustainable businesses that are great for customers and generate healthy profits for the owners. His best-selling book, Rework , shared his practical approach for entrepreneurs. In this wide-ranging interview, Jason discusses these important topics: How the core principles of Basecamp remain focused on simplicity and essential tools for project management after 20 years. Why Basecamp targets small businesses, avoiding the enterprise market that many competitors chase. Why software should fit the needs of the user, rather than forcing users to adapt to complex tools for big companies How profitability, not growth, provides the freedom to innovate and explore new ideas. Why competing against your costs is more important than competing against other companies. How small teams have the agility to win against big companies. Quote from Jason Fried, co-founder and CEO of 37signals “My sense of independence has always been important to me. That’s why I became an entrepreneur: to do things the way I wanted to do them. Otherwise, why be an entrepreneur? It’s true when you work, you’re working for your customers. That’s always going to be true. But you still have a sense of independence. You get to make your own decisions. “What people don’t realize is when you raise money, you don’t really work for yourself anymore. You really don’t. You work for someone else’s schedule, for someone else’s fulfillment, for someone else’s return. That never appealed to me. “I want our products to explain themselves. I want our success to explain ourselves. I don’t want to have to explain myself on a quarterly basis to somebody who’s trying to get a return out of me. I’m not interested. So for all those reasons, it just wasn’t right to raise big funding.” Links Jason Fried on LinkedIn Jason Fried on Twitter 37Signals on LinkedIn 37Signals website Basecamp website HEY website Ruby on Rails website Podcast Sponsor – Full Scale This week’s podcast is sponsored by Full Scale , one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.…
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Practical Founders Podcast
1 #125: Created the World’s Largest Subscription Service for Creative Design – Russ Perry 1:08:10
1:08:10 Play Later Play Later Lists Like Liked1:08:10
Play Later Play Later Lists Like LikedQuote from Russ Perry, founder and CEO of Design Pickle “The game for practical SaaS founders really comes down to recognizing that there is a large market size for very boring niche companies. Finding that niche is the fastest path to success. Don’t be afraid to be boring and specific. “If I were to do Design Pickle all over again, I would have just picked a vertical niche, like we are the graphic design provider for feline mobile cutting trucks or something. There are easily 10,000 mobile pet grooming businesses in the United States, so probably just cat groomers. “We just went super broad when we started, and it’s been fine, but it would have been easier for us to have focused on a niche. When you have such limited resources and time and money and capital, having that narrow niche makes it easier to maximize all those dollars and investments.” Links Russ Perry on LinkedIn Design Pickle on LinkedIn Design Pickle website Colorado River Partners Podcast Sponsor – Full Scale This week’s podcast is sponsored by Full Scale , one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel . Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.…
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Practical Founders Podcast
1 #124: From Services to SaaS Products to a Successful Acquisition in India - Sunando Bhattacharya 1:05:41
1:05:41 Play Later Play Later Lists Like Liked1:05:41
Play Later Play Later Lists Like LikedSunando Bhattacharya spent 13 years as a business leader in managed IT services companies in India before starting his own cloud tech services business. This company grew slowly and an opportunity arose to create a software product for one of their clients. Two years later, in 2019, they had a few more Apiculus product customers and focused more on the product. Apiculus is a complete "cloud-as-a-service" software platform for data centers to offer, sell, deploy, and manage cloud data services for their own customers. They focused on smaller data centers in emerging markets, including Nepal, Oman, Rwanda, and others in the Middle East and Africa. The Apiculus business grew as it turned into a product-first company. They overcame many challenges during COVD and with customers and partners that didn't work out. In 2024, the company was acquired by Yotta, and Indian cloud technology company, in a strategic acquisition. Quote from Sunando Bhattacharya, founder of Apiculus "Somebody asked me what one thing you want for your company. I said I wanted my company featured on Great Places to Work. It's very important that the team that works with me finds this a great place to work. "The only secret ingredient for tech companies is people. It's people who make the technology. And if you take care of your team, you take care of your people, you will always do well. "This isn't just for services companies. Talent and ability are important. But for somebody to bring their best every day to work and deliver something world-class, which is world-beating, it needs a very different level of passion. And that passion will only come from your team if you take care for them." Links Sunando Bhattacharya on LinkedIn Apiculus on LinkedIn Apiculus website Yotta Data Services website Podcast Sponsor - Cypress Growth Capital This week’s podcast is sponsored by my friends at Cypress Growth Capital . For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.…
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Practical Founders Podcast
1 #123: How Practical Founders Are Winning Big with Growth Equity Funding – Growth Street Partners 57:37
57:37 Play Later Play Later Lists Like Liked57:37
Play Later Play Later Lists Like LikedSteve Wolfe and Nate Grossman are co-founders at Growth Street Partners , a growth equity firm focused on investing in early-stage B2B SaaS companies between $2M-$6M in ARR. They discuss how growth equity funding works for SaaS founders and how it allows entrepreneurs to maintain control while still benefiting from investment and liquidity. In this expert episode, Steve and Nate get specific and share real examples of how SaaS founders use growth equity to win bigger, when it can be a good fit for founders, and how founders scale their businesses and win with multiple exits. They also describe: Why Growth Street Partners focuses on practical founders with growth equity. How growth equity is different from traditional private equity and venture capital. Why successful founders are “learn-it-alls” with a growth mindset. How founders can achieve multiple exits through strategic partnerships. Why building a strong team is essential for scale-up success. Quote from Steve Wolfe, co-founder of Growth Street Partners “We know that when entrepreneurs have fun, their companies do much better. When founders continue to feel real ownership in their business and in the success of their company, they do a lot better, too. “So we set up our whole firm to enable that. We are investing to own just 20% to 50% of a business, so the founder still controls the company. We go to them with execution ideas and proven frameworks and approaches, but we are really just giving them the tools to make better decisions themselves. “They know they make the decisions in the end, so they will make sure that it’s successful. There’s something beautiful about that relationship and about helping that founder get to where they want to go while still feeling like they did it.” Links Steve Wolfe on LinkedIn Nate Grossman on LinkedIn Growth Street Partners on LinkedIn Growth Street Partners website Podcast Sponsor – Full Scale This week’s podcast is sponsored by Full Scale , one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.…
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