Practical Founders Podcast

Greg Head
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Nov 17, 2023 • 1h 10min

#70: Bootstrapped to $3M and Raised a VC Round Before a $200M PE Transaction – Jafar Owainati

Jafar Owainati was a mechanical engineer before he got an MBA in entrepreneurship and decided to start a software company with two friends. They looked at many ideas before building software to help sales engineers respond to Requests for Proposals (RFPs) faster and easier. They launched Loopio in 2014 and had paying customers within one year. The three founders built the software and sold the first customers before adding more employees as they approached $1M ARR. They kept growing faster with a disciplined and frugal approach to $3M ARR before raising a round of VC funding from OpenView Ventures, a practical investor that aligned with the vision and approach of Loopio's founders. Loopio now has hundreds of employees and Sumeru Equity Partners made a strategic $200 million private equity investment in 2021. Jafar left to start a compensation management software company called Barley which is starting to grow quickly now. Learn more at practicalfounders.com.
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Nov 10, 2023 • 1h 11min

#69: Bootstrapped a Fintech Payments Platform to $10M ARR in 3 Years – Miles Schwartz

Miles Schwartz a cofounder of Zūm Rails, a fast-growing fintech based in Canada with a growing worldwide presence. In just 3.5 years and without any outside funding, Zūm Rails has grown from a focused startup to a credible open banking and instant payment gateway with $10M in ARR. Zum Rails also integrated KYC (Know Your Customer) technology which reduces fraud across all payment types. Miles and his cofounder had experience with fintech payments before they started Zum Rails to improve EFT payment processing in Canada. As they worked with more partners and grew revenues, they expanded the Zum Rails solution and built relationships with larger partners. Fast-growth, larger partner opportunities, and traction with a US expansion are causing Miles and his cofounders to think differently about the potential for the company and potentially raising growth capital from the right VC investment partner. Learn more at practicalfounders.com.
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Nov 3, 2023 • 1h 11min

#68: Bootstrapped and Sold a Successful Startup in Latin America – Bernardo Carvalho Wertheim

Bernardo Carvalho Wertheim, founder of The Bridge, shares his journey of building a successful tech startup in Latin America. Topics discussed include the challenges of operating in Latin America, the impact of COVID-19 on the digital talent market, and the transition from startup to a big company.
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9 snips
Oct 27, 2023 • 1h 2min

#67: Grew and Sold a Profitable Healthcare Software Company – Patrick Randolph

When Patrick Randolph discovered that doctors' offices lose 20% of appointments due to patient cancellations and no-shows, he set out to design and test a solution. QueueDr was created to fill those open slots with patients in the waitlist "queue." With just a little funding and lots of hard work, they began by helping small practices and group practices fill open slots with no human intervention. Eventually, they sold to larger organizations and became profitable as they grew. QueueDR was acquired by Phreesia (PHR: NYSE) in March 2021 for an undisclosed amount. Topics discussed on this podcast How he prototyped and designed the full product before writing any code The multiple challenges of selling technology to healthcare providers How they started by selling to small offices and eventually sold enterprise deals to large organizations Why he didn't want to raise another round of VC funding after raising $1 million from an investor How he developed the relationship with leaders at the company that eventually acquired QueueDr How he thinks about life after selling his company Learn more at practicalfounders.com.
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Oct 20, 2023 • 1h 7min

#66: Serial SaaS Founder Had Three Successful Exits in Three Different Ways – Raj Khera

Raj Khera has had three exits as a software entrepreneur and leader in his long career. His first company, GovCon, grew in the late 1990s to help government contractors easily access new contracts up for bid by the US government. Their advertising and subscription revenues grew quickly, and he sold GovCon in 1999 for $12.5 million. He bootstrapped one of the first email marketing software businesses in the early 2000s called MailerMailer to help small businesses send emails. Raj and his brother Vik ran this as a profitable small business for many years, giving them an interesting business challenge while not sacrificing time with their families. After running the business for 15 years, Raj sold MailerMailer to a public software company, J2 Global, in 2017. Then Raj joined a struggling VC-funded software company called WealthEngine to help grow sales, create new products and exit. Wealth Engine was successfully sold in late 2020. Raj is now an active advisor to software founders. At MoreBusiness.com, he coaches software founders to efficiently acquire customers using advanced search engine optimization and marketing techniques. Learn more at practicalfounders.com.
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Oct 13, 2023 • 1h 12min

#65: The Bootstrapped Rocket-Ride Success Story of HighLevel – Robin Alex

Robin Alex worked in a digital marketing agency in Dallas when he discovered their small business clients struggled to nurture and follow up with their website leads. In 2018, Robin and two developers prototyped a marketing automation and CRM software that could help other agencies solve this problem for their clients. They pitched the product and got a great response. They built their first product and HighLevel grew quickly. HighLevel grew fast as word of mouth and referrals spread in the agency community. HighLevel is an all-in-one sales and marketing platform for agencies that serve small businesses. With marketing automation, CRM, and payment tools, HighLevel has an innovative "white-label" platform that their agency customers rebrand to deliver custom solutions to their customers. HighLevel has over 60,000 agency customers, over 3 million small business users, and over 700 remote employees. HighLevel is adding 30-50 employees a month, yet they are still "moving fast and breaking things" to move fast and serve their agency customers. The founders took a practical growth equity round of funding in 2021 from PeakEquity. Learn more at practicalfounders.com.
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Oct 6, 2023 • 59min

#64: Bootstrapped, very profitable and still having fun after 18 years – Mike Roberts

Mike Roberts is the founder and CEO of SpyFu, a leading competitive research tool for marketers and entrepreneurs with over 15,000 paid customers and hundreds of thousands of free users. SpyFu was launched in 2006 and has been a profitable and bootstrapped business for almost 18 years. Mike is a happy founder who splits his time between leading the business and his personal pursuits, which include surfing and spending time with his family. He is still passionate about innovation, search marketing technologies, big data and AI, and creating new ways to help smaller businesses succeed. Learn more at practicalfounders.com.
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Sep 29, 2023 • 55min

#63: Successfully Scaling Up a Bootstrapped Vertical SaaS Business – Raution Jaiswal

Raution Jaiswal grew up in India and then worked in management roles at large companies in the US before he discovered a problem experienced by small insurance agencies. He validated the problem, built an early solution, and didn't quit his full-time job in 2018 until he had 50 paying customers. InsuredMine provides an all-in-one sales CRM (customer relationship management) and marketing automation software for independent insurance agencies in the US. InsuredMine helps improve and automate marketing, sales, and service to help insurance agencies sell more, serve customers better, and become more profitable. It also integrates with many popular agency management systems (AMS). The bootstrapped company is growing up quickly with almost 60 employees, a leadership team, and a growing reputation. In addition to over 1,000 small insurance agency customers, InsuredMine is now being used by some of the largest agency organizations in the US. Learn more at practicalfounders.com.
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Sep 22, 2023 • 56min

#62: She Quit Her CPA Job to Create This Fast-Growing SaaS Startup – Kelly Mann

Kelly Mann was a CPA and auditor for 15 years before leaving her employer to start her own CPA firm focused on 401K benefits audits. She discovered a need to automate this process, validated the market with other CPAs, and created the first AuditMiner software. Unfortunately, Kelly was diagnosed with Stage 3 breast cancer just before launch and started aggressive chemotherapy immediately. After a year of treatment, AuditMiner was launched, and CPA firms lined up to buy it. With her treatments and surgeries behind her, Kelly is now CEO of a fast-growing and profitable SaaS software company with 15 remote employees, hundreds of customers, lots of publicity, and suitors interested in buying the company. Kelly openly shares her personal journey with cancer and how she thinks differently about running a software company than most founders. Learn more at practicalfounders.com.
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Sep 15, 2023 • 1h 11min

#61: Sold His Bootstrapped SaaS Company for 16X Revenues - Praveen Ghanta

Praveen Ghanta, Co-founder and former CEO of Hidden Levers, shares his entrepreneurial journey from MIT graduate to bootstrapped SaaS success. He reveals the strategic decisions that led to selling Hidden Levers for an impressive 16X revenue. Praveen discusses the challenges of transitioning from corporate life, building a product to serve wealth managers, and the advantages of using fractional teams for growth. Now at the helm of Fraction, he emphasizes nurturing talent and practical insights for aspiring founders in the SaaS landscape.

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