Practical Founders Podcast

Lloyed Lobo is the co-founder and former president of Boast.ai, a leading platform to help software companies in the US and Canada to redeem available government tax credits. Initially started in 2012 as a services business helping companies administer tax credits, Boast.ai was launched as a technology-powered platform that scaled their business much faster.

Technology-powered Boast.ai was launched in 2017 after starting a services business in 2012 that helped larger company administer their R&D tax credits. Boast.ai bootstrapped their growth to $10 million ARR before taking an investment from Radian Capital that also allowed Lloyed and his cofounder to cash out some of their equity for life-changing cash payouts. Their growth was fueled by the active startup community they built called Traction.

Lloyed faced many challenges as an immigrant, startup adventurer, frugal entrepreneur, and hyperactive community builder. He also struggled after the investment when he finally had monetary wealth and experienced depression. With the support of his family and therapy, he moved forward to prioritize his health and family and limit his startup addiction.

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Ryan Goodman joined the startup in the early days of the business intelligence and analytics market in 2003 as a specialist helping large customers adopt this new technology. This startup was acquired by the successful BI company Business Objects, which was then acquired by the huge software company SAP. Ryan left to start consulting and build niche add-on "feature products" in the SAP Business Objects ecosystem.

They experimented with product ideas and consulting services before finding an opportunity to help Business Objects users easily visualize data on Google Maps. They grew fast as an add-on product selling to large companies all over the world, reaching 700 customers and $1.4 million ARR. But new BI platforms and technology changes slowed their growth and completely changed the market opportunity.

Ryan talks about the pivots and experiments they tried before deciding to shut down the company and sunset their core product. He shares his difficult decision process and the emotional journey, including lessons learned and perspective gained in hindsight.

In this episode, Ryan explains:

• How he started in the pioneering early days of business intelligence and analytics for big customers
• Why he left SAP after being acquired twice to start his own add-on software business in the Business Objects community
• How he experimented and survived long enough to find a compelling product opportunity that quickly grew to over $1M ARR
• How the market changed and how that eventually led him and his cofounder to shut down the business slowly
• How he feels about the successes and failures of his software startup journey

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As the host of the Practical Founders Podcast, I have interviewed 46 successful SaaS founders and 6 savvy experts in the first year of weekly episodes. In this episode, I share some of the deeper insights, surprising lessons, and useful perspective that I have learned after so many great conversations.

Practical founders are building valuable software companies without big funding all over the world and in every corner of the software business. It's an amazing time to be a practical founder. Practical founders are solving problems, changing the world, and doing it their way.

The founder equity value and founder wealth created by just the 46 founders I interviewed this year is over $1 billion. Tune in to this episode where I share what's going on right now and how these founders are succeeding in their own ways.

In this episode, Greg explains:

• What characteristics that all successful practical founders have in common
• Why there are so many variations and ways to create a successful software company when you don't raise big funding
• What has happened in the last 5 years that makes it better for most new founders to grow a serious software company without big funding
• Why we don't see the hundreds of billions of founder equity value and wealth that have been created by practical founders who have grown thousands of valuable software companies without big funding

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Patrick Fingles grew a successful roofing company with hundreds of employees in the Baltimore-Washington DC area. In 2013, they created their own software to help new salespeople estimate, quote, and close new roofing sales. They started selling the software to other contractors in 2016 and called it Leap.

Leap grew fast to $7 million ARR in 2021 with Patrick as the CEO. In 2021, they decided to take some growth funding from Nexa Equity to give Patrick and his cofounders their "first bite" of successful liquidity and support future growth and acquisitions.

Leap is now the leading contractor management software with CRM, project management, and point-of-sale functionality specifically designed for the unique needs of home improvement contractor and remodelers in the U.S. Leap is now over $20 million in ARR with over 150 employees and full-time contractors and is still growing fast.

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Jordan Fleming grew up in Toronto and New York, then lived in Edinburgh, Scotland for 15 years where he created a successful consultancy helping larger businesses automate and improve their processes. His experience developing workflow apps led him and his cofounders to create a tightly-integrated phone system solution called smrtPhone built just for the Podio workflow platform, which is very popular in several industries. Jordan now lives in Poland and most of the team works in their office in Romania.

The bootstrapped and profitable smrtStudio Global company is now growing fast with 2400 customers, 45 employees, and nearly $5 million in ARR (annual recurring revenue). They are very disciplined about company culture, building a scalable organization, growing employees, and preparing for growth before problems arise.

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Gregory Shepard is a serial entrepreneur who has created and sold 12 companies, including marketing software and ad technology companies. In 2016, he sold two of his bootstrapped software companies, AffiliateTraction and AdAssured to eBay for an undisclosed "f*ck-ton of money," as he describes it. He is now an author, speaker, philanthropist, investor, and the creator of Startup Science and BOSS, an open-source business operating system to help more startups succeed.

Gregory faced monumental challenges as a child growing up in poverty with a rare combination of autism, dyslexia, synesthesia, savant syndrome, and other neurodivergent conditions. He learned to develop himself and overcome big challenges, including creating, growing, and running many software companies over three decades.

In this interview, Greg shares his difficult personal challenges and his successful entrepreneurial journey as an experienced practical founder. He also shares several powerful insights and approaches for bootstrapped software founders that you won't hear from investors or the current startup education.

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Deepak Sindwani is a former software entrepreneur who has been a professional investor in software companies for over 20 years. Deepak is the co-founder and managing partner of Wavecrest Growth Partners, a growth equity investor in practical B2B SaaS companies. Wavecrest specializes in helping bootstrapped and capital-efficient founders of vertical B2B SaaS companies reduce risk and grow their companies from $5M-$10M ARR to $30M-$50M ARR and drastically increase the value of their companies.

Growth equity funding is a practical version of institutional funding that is different than traditional "Get Big Fast At All Costs" big venture capital approach. With more reasonable growth and exit expectations, more help for founders and their teams, and more secondary for founders (to take some money off the table), growth equity partners can help ambitious founders scale their impact with an efficient approach. Unlike private equity (PE) majority acquisitions and "roll-ups", growth equity investors want to grow businesses organically and support the founders in their journeys.

This is an expert interview in which I ask Deepak to educate us about the growth equity funding game and answer typical questions for founders who are considering taking on a funding partner to efficiently accelerate growth after they reach $3M-$5M ARR.

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Sam Knight is the co-founder and former president of BOLT Software, a project management and scheduling software for the construction trades that build residential homes. Sam helped lead the BOLT team as it grew before the company was sold and now he guides the BOLT product in the larger company.

BOLT was created in 2015 after years of internal use at a large Dallas-based electrical contractor. Cofounder Josh Causey brought in Sam Knight to spin out and run BOLT as a separate software company and grow the customer base and improve the product. Through 2020, the company grew to over $1M in recurring revenues before it was acquired in 2020 by Fort Worth-based ECI Solutions to expand its construction software offering.

Built by the trades for the trades, BOLT is a SaaS solution that simplifies project management, scheduling, and estimating for new home construction subcontractors (electricians, painters, plumbers, etc.). BOLT helps those subcontractors truly manage their teams: from rescheduling due to unforeseen delays to scheduling out multiple crews simultaneously.

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Chris Kern is an expert independent M&A advisor who has helped over 150 growing tech companies get financing, obtain investment, or sell their companies. He is Managing Director of Windstream Partners where he advises smaller SaaS and tech business owners in selling their companies for successful exits between $10M-$50M.

Chris got his start on Wall Street working on large finance and acquisition deals, but he quickly shifted gears 20 years ago, moved to Phoenix, and started working only with small software companies with growing SaaS, software, and technology businesses. I have known Chris for over 15 years.

In this interview with an active M&A professional who helps many practical SaaS founders sell their companies every year. I ask Chris the most common questions I hear from practical founders who are thinking about selling their companies someday.

"There are a thousand times more companies getting acquired for less than $50 million than all of those that sell for billion-dollar valuations. You just don't hear about these deals because they are smaller and often have confidentiality agreements in place," Chris explains.

In this episode, Chris explains:

• What's happening right now in mergers & acquisitions of software, SaaS, and fintech companies that sell for $10M to $50M?
• What are common valuations ranges for software startups and small companies with revenues between $500K and $5M in ARR?
• What are the factors that affect valuation one way or the other?
• Can you really sell a startup for a multiple of revenues when it's still small?
• Who is buying these smaller software companies and why are they buying them?
• What is the general process of selling your company?
• What should they be thinking about before they try to sell to maximize their outcome?
• Is it better to have outside funding or to have bootstrapped when selling your company?

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Joshua Strebel started a small SEO and website agency in the early 2000s after graduating from university. Joshua and his wife Sally experimented with website hosting using WordPress with low monthly fees while they ran their services business in Scottsdale, Arizona. WordPress became popular and eventually Pagely was formally launched as the first managed WordPress hosting platform in 2009 and they closed their services. business.

Pagely grew steadily until 2013, when dozens of inexpensive managed WordPress hosting competitors entered the market, all backed by big VC funding. Pagely was bootstrapped with no outside funding, so they slowly changed their focus to serve only the biggest companies the largest WordPress sites with the most complex needs. Pagely revenues grew 1000% in just 3 years after focusing on the top 1% of WordPress customers.

Pagely was profitable and sustainable with many big-brand large customers when they sold the company in 2021 to GoDaddy, the huge website hosting company also based in Arizona. With nearly $10 million in ARR, Pagely's strategic exit created generational wealth for Joshua and Sally and life-changing wealth for multiple key employees.

Learn more at practicalfounders.com.,