Practical Founders Podcast

Blakely Graham co-founded TaskRay, a project management and customer onboarding platform built inside the Salesforce ecosystem. After years working with Salesforce implementations and operations teams, she and co-founder Eric Wu saw a major gap between closing deals and successfully onboarding customers. They bootstrapped the company from a simple Kanban-style workflow app into a growing SaaS business serving increasingly complex enterprise implementations.

TaskRay started with self-serve AppExchange purchases and evolved into enterprise software with six-figure contracts, serving companies with sophisticated onboarding and delivery needs. The company stayed profitable from the beginning, grew to roughly 40 employees, and eventually reached nearly $10M ARR. A major turning point came when the team repositioned around "customer onboarding" instead of generic project management, dramatically improving focus, retention, and enterprise growth.

Blakely also shares the difficult founder realities rarely discussed openly: co-founder conflict, burnout, loneliness, identity shifts, and the emotional weight of leading a growing company for more than a decade. After stepping away following the 2021 sale of TaskRay to a search fund-backed buyer, she focused on recovery, advisory work, and co-hosting the Not All Business podcast to help founders and leaders feel less isolated during difficult growth stages.

Key Takeaways

• Focus to Grow Faster — TaskRay discovered its strongest positioning by focusing narrowly on post-sale onboarding instead of generic project management.
• Bootstrap Discipline — The company stayed profitable from day one by growing carefully, shipping quickly, and avoiding unnecessary complexity early.
• Founder Burnout — Burnout showed up as physical exhaustion, emotional numbness, and losing the energy to inspire teams or create new ideas.
• Co-Founder Conflict — Long-term founder relationships can fracture under pressure, but respect and self-awareness can rebuild trust over time.
• Invest In Yourself — Peer groups, coaching, therapy, and personal health practices are essential leadership tools, not optional luxuries.

Quote from Blakely Graham, Co-founder of TaskRay

"This is probably the most important thing I learned as a CEO, and, I swear founders can't hear it. They just can't hear it.

"You have to invest in yourself. The word "self care" drives me crazy because that's what people told me for 10 years. Self care. What are you doing for self care? I'm like, I don't know. Leave me alone. I don't have time, any down time.

"Well, of course sitting on the other side of burning out and selling my company, founders just have to invest in themselves in the journey. It can be a peer group, it can be a coach. can be therapy. Heck for me, it's nature walks and going to the gym. Just do it because people don't want you to burn out. They want your leadership, so you have to invest in yourself and don't feel guilty about it. There, I said it."

Links

• Blakely Graham on LinkedIn
• TaskRay on LinkedIn
• TaskRay website
• Plexus Capital website

LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned.

If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system.

Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools.

Visit launchbay.com/practical and get 25% off your first 3 months on any LaunchBay plan.

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.

Practical Founders CEO Peer Groups

Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Andy Alsop didn't start The Receptionist—he bought a small iPad-based visitor management app in 2013 for $250K and turned it into a real SaaS business. What began as a simple front-desk check-in tool evolved into a full visitor management system used across offices, schools, and manufacturing sites.

Over a decade, Andy grew the company to 5,500 customers across 8,000 locations and more than $7M in ARR with just 30 employees. He stayed mostly bootstrapped, focused on steady growth, strong customer retention, and a unique "employee supremacy" culture that emphasized trust, transparency, and long-term loyalty.

At an inflection point—needing more capital to keep up with a maturing market—Andy chose to sell rather than raise growth equity. The company was acquired by Sign In, a growth-equity-backed platform consolidating the category. In this episode, Andy shares how he evaluated buyers, avoided common exit traps, and built a company worth acquiring without chasing VC growth.

Key Takeaways

• Simple Product, Deep System: What looks like a basic iPad app becomes complex, sticky infrastructure with integrations, compliance, and workflow depth.
• Bootstrap Leverage: Growing with customer revenue forced discipline, creating a profitable, efficient business attractive to strategic buyers.
• Employee Supremacy Works: Trust, transparency, and benefits (like every-other-Friday off) drove retention, performance, and long-term value creation.
• Clean Books Matter: Meticulous financial discipline prevented retrading risk and made due diligence smoother and more favorable.
• Exit Optionality Wins: Not needing to sell created leverage—allowing Andy to choose the right buyer instead of taking the only offer.

Quote from Andy Alsop, CEO of The Receptionist

"I sold 100 % of the company. It was a full acquisition. I wasn't even looking for, and this is something that my brother in tech always said: Don't build a company to sell it, build a great company and somebody will want to come along and buy it. And I think that's exactly the way it played out. We didn't go and look for the acquisition. We were pursued by Sign In and that's what happened.

"Just build a great company and somebody will want to come along and buy it. Because I didn't want to just sell it. I mean, we're profitable. We're growing. We have very low churn. Great employees. We're doing great in the marketplace, I didn't really have to sell."

Links

• Andy Alsop on LinkedIn
• The Receptionist on LinkedIn
• The Receptionist website
• Sign In website

This podcast is sponsored by Lighter Capital.

In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.

Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period.

Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.

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.

Practical Founders CEO Peer Groups

Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Sharon Nouh built ProSpend, a spend management SaaS platform for mid-market companies, after seeing firsthand how broken expense processes were in corporate travel. Starting with an expense tool, focused on her home market in Australia, she bootstrapped the company and landed a global enterprise as her first customer with a simple but powerful product vision.

Over 10 years, she expanded ProSpend into a full spend management system covering expenses, accounts payable, purchase orders, and budgets. The company grew to about 1,000 customers and 50 employees, with annual contracts ranging from roughly $15K to $40K, driven by strong mid-market focus and channel partnerships.

In 2025 Sharon sold ProSpend to ISH (Invincible Software Holdings), a strategic acquirer. She still runs ProSpend but can now accelerate expansion into the UK. After years of staying independent, she chose a acquisition partner over VC funding to maintain control and execute her long-term vision, showing how a sale can be a strategic move—not an endpoint.

Key Takeaways

• Bootstrap Reality — It took five to six years before taking meaningful income, with constant cash flow pressure early on.
• Product Expansion — Growth came from adding adjacent modules CFOs needed, not chasing unrelated features or markets.
• Channel Leverage — Partnering with MYOB and resellers now drives about 50% of new customers efficiently.
• Control Matters — Avoiding VC preserved full control over timing and terms of exit decisions.

Quote from Sharon Nouh, CEO and Founder of ProSpend

"A couple of years ago, one of the visions that I had for ProSpend was to expand from Australia into the UK. The UK was always going to be the market that we wanted to move into, rather than the US, because it's a very aligned, very similar market.

"And also because one of our competitors, WebExpenses, had been bought and sold about four times, and they were the incumbent in the UK. They were suffering. They hadn't been developing their product. There was a real gap for us to go into the UK and start picking up the mid-market there.

"So the question was, do I get VC funding, even though we've always been bootstrapped. Or do I look for an acquiring partner, somebody from the UK who could take us in there with boots on the ground and market intelligence? And I chose the latter and sold the business that I still run."

Links

• Sharon Nouh on LinkedIn
• ProSpend on LinkedIn
• ProSpend website
• ISH website

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.

Practical Founders CEO Peer Groups

Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Perry Rosenbloom, founder of LaunchBay, previously built and sold Brighter Vision before starting his second SaaS company focused on onboarding. After running hundreds of onboarding processes per month, he saw a consistent problem: what happens after the sale is messy, manual, and often ignored.

LaunchBay helps SaaS and professional services teams manage customer onboarding with structured workflows, shared client portals, and automation. The company has grown past $1M in ARR, doubling in 2025, with a focused approach on helping teams reduce onboarding time from 60–90 days to significantly faster activation.

Perry shares practical lessons on onboarding as a core growth lever—not just an operational task. He explains why onboarding debt compounds, why charging for implementation improves outcomes, and how better onboarding drives retention, expansion, and long-term revenue quality.

Key Takeaways

• Onboarding Debt Compounds - Most SaaS companies duct-tape onboarding early, but delays, inefficiencies, and churn risks compound quickly as sales scale.
• Activation Matters More - The real bottom of funnel isn't closed-won deals—it's when customers actually reach value and start using the product.
• Stop The Chase - Much of onboarding is manual follow-ups and coordination; removing this admin work unlocks higher-leverage customer success teams.
• Charge For Setup - Charging for onboarding improves completion rates, sets expectations, and ensures customers have real skin in the game.
• Segment The Process - Treating all customers the same breaks onboarding—different tiers and workflows are required for different customer types.
• Visibility Is Critical - Without clear visibility into onboarding progress and bottlenecks, problems are only discovered after deals are already at risk.

Quote from Perry Rosenbloom, Founder of LaunchBay

"There's only so long that you can duct tape a process like onboarding new customers, with just hustle to make it work. A lot of companies are using Google Docs, shared Slack spaces, shared spreadsheets, and it almost works, until it doesn't. And the biggest mistake is continuing to let it not work.

"When you're founder-led and you are doing one to three implementations a month, you can get by without a dedicated tool for that. It's not going to be the best customer experience, but you can get by without a tool for that.

"But when you want to start scaling, you need to build out repeatable processes that can enable every single customer to have a phenomenal experience that is consistent, that is unified and that delivers value. "That's when you start looking for a specialized solution to solve those problems and don't build up more onboarding debt. Onboarding debt is real and early-stage SaaS companies in their processes and customer experiences."

Links

• Perry Rosenbloom on LinkedIn
• LaunchBay on LinkedIn
• LaunchBay website
• Free ebook: The Paid Implementation PlaybookROI calculator: Implementation margins

LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned.

If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system.

Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools.

Visit launchbay.com/practical and get 25% off your first 3 months on any LaunchBay plan.

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.

Practical Founders CEO Peer Groups

Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Dina Nagalla built EmpowerMX over more than a decade to digitize aircraft maintenance for major airlines like American, Southwest, and United. Starting from deep domain experience inside aviation IT, he tackled a complex, high-stakes problem—replacing paper-based processes with a full execution system that improves efficiency and compliance.

The company grew into a mid–double digit SaaS business serving global airlines with contracts ranging from hundreds of thousands to several million dollars annually. With a lean early team and offshore development, EmpowerMX delivered measurable ROI—often saving customers 10% or more on maintenance operations—while expanding globally with growth equity support.

After surviving COVID (when revenue briefly dropped near zero) and accelerating post-pandemic digitization, Dina sold the company to IFS. He chose to exit not out of necessity, but to pursue a new purpose—now building multiple AI-driven products focused on improving human outcomes like mental health and education.

Key Takeaways

• Vertical Expertise Wins: Deep domain knowledge created credibility and trust—critical for selling into conservative, high-risk enterprise environments.
• Start Small, Scale Smart: Initial product built with ~12 people, proving capital efficiency can solve very large industry problems.
• ROI Sells Enterprise: Clear financial impact (10%+ cost savings) overcame skepticism and justified multi-million dollar contracts.
• Trust Over Features: Adoption depended more on frontline trust than functionality—especially replacing paper and manual workflows.
• Purpose Drives Exit: Founder sold from a position of strength, driven by personal direction—not investor pressure or company distress.

Quote from Dinakara Nagalla, President and CEO of EmpowerMX

"Why did I sell the company when it was doing well? Life happens, you know. Primarily it was a desire driven by me that I want to do something different. So do I look back and think about it? Yes, I do.

"It's just that my purpose in life kind of switched. I wanted to do more meaningful things. I wanted to do more things. We were extremely profitable the year we sold and my equity partners were really happy with how things were going. "When I exited I moved right into building new products with new teams. So I didn't like take a step back and said I need a week of break. I think I had better vacations with my family when I was still running the company. Right now I'm doing, I get up at three o'clock in the morning. I work till four in the evening.

"You know, there is always this thing I hear from people all the time in my last 27 years of being in US: If you like what you do, you're not working another day. I think that is true in my case. I truly love what I do. Even when it's hard."

Links

• Dinakara Nagalla on LinkedIn
• EmpowerMX on LinkedIn
• EmpowerMX Website
• IFS website

This podcast is sponsored by Lighter Capital.

In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.

Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period.

Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.

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.

Practical Founders CEO Peer Groups

Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Chad Ingram is the founder of Distro, an AI recruiting software company that helps mid-market and enterprise companies automate candidate screening, vetting, ranking, and scheduling. He previously built Jump, a venture-backed customer engagement software company, through a stressful growth and sale process that taught him painful lessons about fundraising, control, and acquisition pressure.

Distro started as a marketplace to help companies hire software engineers globally, then evolved into an AI-first recruiting platform that integrates with applicant tracking systems and helps recruiters handle far more open roles. When Chad sold the company,

Distro had 14 employees and about $3.5M ARR, with revenue shifting from marketplace margins toward SaaS subscription and consumption-based contracts. Distro was acquired by Vensure Employer Solutions, a large private HR platform company that wanted Distro both for its own recruiting needs and for its 161,000 customers.

Chad explains why strategic buyers cared more about healthy financials than SaaS vanity metrics, why he said no to the first offer, what he learned from selling Jump too early, and why a daily cash flow forecast gave him the freedom to choose instead of react.

Key Takeaways

• First Offers are not always the right offers, and founders with real options can politely say no and keep building.
• Manual First is often the smartest way to start, proving demand with spreadsheets, email, and humans before writing software.
• Product Evolution happened by following customer demand, turning a hiring marketplace into an AI recruiting SaaS platform.
• Cash Visibility gave Chad optionality, because daily cash flow tracking removed surprises and helped him make harder decisions earlier.

Quote from Chad Ingram, founder of Distro

"You gotta know your numbers in detail. There are so many founders who don't know their freaking numbers. How do you not know your numbers? You just hope it all works itself out in six months? That's not how it works. You will go out of business.

"I learned how to do a daily cash flow forecast when we started my 2nd company, Distro. And I've been running one every day. That might seem a little too microscopic for many, but guess what? There's no freaking surprises.

"I could tell you nine months from now, the day that we would go out of business if we didn't have enough cash, unless there was some change. It's a lot less stressful knowing the facts. When you know the facts, you can make things happen. You don't have to sit and wonder and hope it works out.

"I don't care if you have zero mathematical aptitude or your background is sales or something else. You have to know the basics of accounting. If you don't, you are at a huge, huge disadvantage, especially when you go to sell."

Links

• Chad Ingram on LinkedIn
• Distro on LinkedIn
• Distro website
• Vensure Employer Solutions website

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.

Practical Founders CEO Peer Groups

Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Joseph Lee is the co-founder and CEO of Supademo, a fast-growing SaaS company solving a common pain: quickly creating new product demos. In just two and a half years, they built a modern, AI-powered solution that dramatically simplifies how teams showcase software.

Supademo has reached $3M ARR in 2.5 years and is growing more than 100% annually with a freemium model. The product enables teams to create interactive, annotated, and even translated demos in minutes instead of days or weeks. The freemium model, reverse trial onboarding, and viral product loops have driven strong PLG growth, while enterprise demand is now emerging as a second growth engine.

Joseph is a second-time founder with global experience from Korea to Vancouver to New York. He's raised a small amount of capital but is focused on practical execution. His approach reflects tghe broader shift of using AI to solve real workflow bottlenecks and grow efficiently without heavy funding.

Key Takeaways

• Speed Wins - Reducing demo creation from weeks to minutes unlocks more usage, faster iteration, and better customer understanding
• Do The Work - Early traction came from building demos for prospects manually, removing friction and proving value instantly
• Reverse Trials - With free plans drive high conversion by letting users experience full value before choosing a plan
• PLG + Enterprise - Bottom-up growth creates stability, while enterprise deals add larger revenue but less predictability
• Constant Reinvention - Product-market fit is temporary in AI—founders must ship fast, iterate weekly, and stay paranoid

Quote from Joseph Lee, Co-founder and CEO of Supademo

"There's no bread and butter GTM channel that is going to work permanently into the future. And the biggest learning that I took away was product market fit nowadays has a finite stamp when it comes to a period of time that it's valid for.

"You have to constantly reinvent yourself and be paranoid, because the market is changing, new competition is coming, and the dynamics are changing. You can't rest on your laurels, you got to be constantly innovating, like at a faster pace than ever before.

"Our team competitive advantage is the ability to move quickly and ship quickly. It's combining gut based on our intel and context of the industry and tribal knowledge with some data to act faster than anyone else. Not analysis paralysis or having everything planned out. Just shipping something that may be imperfect, but using that as leverage to learn quickly and iterate quickly."

Links

• Joseph Lee on LinkedIn
• Supademo on LinkedIn
• Supademo website

LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned.

If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system.

Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools.

Visit launchbay.com/practical and get 25% off your first 3 months on any LaunchBay plan.

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.

Practical Founders CEO Peer Groups

Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Tanner Kovacevich of Lighter Capital joins Greg Head to explain how non-dilutive financing works for practical SaaS founders. Since 2010, Lighter Capital has funded hundreds of recurring-revenue SaaS companies that want growth capital without giving up ownership or board control.

Tanner shares discuss how non-dilutive financing fits companies with $1M–$5M ARR that are growing steadily but don't want venture capital. He explains typical loan structures, underwriting factors like churn and revenue trends, and why capital-efficient SaaS companies are often better candidates than "grow-at-all-costs" startups.

We discuss several examples of practical SaaS founders who used debt instead of equity to retain ownership and build long-term value. The conversation focuses on how certain practical founders can use capital strategically—accelerating growth while preserving control and optionality.

Key Takeaways

• Non-Dilutive Capital – SaaS-specific debt financing allows SaaS founders to fund growth without giving up equity, board control, or long-term ownership upside.
• Capital Sequencing – Smart founders combine funding types over time, using non-dilutive capital early before considering equity later.
• Retention Matters – High churn or declining revenue trends are the biggest red flags when underwriting recurring-revenue SaaS businesses.
• Ownership Economics – Avoiding early dilution can preserve tens of millions of dollars in founder equity in successful outcomes.
• Capital Efficiency Wins – Many profitable SaaS companies grow steadily and still attract buyers without needing big VC funding.

Quote from Tanner Kovacevich, VP of Sales at Lighter Capital

"Often we fund founders that just want to have a little more cash on hand and not have to manage cash so closely. What does that open up for the founder's mindset alone? To just have some extra cash on hand, to go out and hire whoever they want, an account executive, SDR. Because a lot of it can be psychological.

"It's not only the grand initiatives; it can just be the ability to breathe, extend your runway to look ahead. Maybe you want to offload a couple of things you're working on as the CEO, like acting as an accountant when you're the strategic CEO and trying to manage sales day to day.

"Lighter Capital provides non-dilutive debt financing for B2B SaaS companies, but we also work with other recurring revenue types of model technology companies. With Lighter, there are no warrants on our loan, no personal guarantees that the founder has to place, and minimal financial covenants on it."

Links

• Tanner Kovacevich on LinkedIn
• Lighter Capital on LinkedIn
• Lighter Capital website
• Bootstrapped Podcast

This podcast is sponsored by Lighter Capital.

In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.

Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period.

Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.

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.

Practical Founders CEO Peer Groups

Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Vivek Bhaskaran is the founder and CEO of QuestionPro, a bootstrapped survey and customer-experience research software platform they have been building for more than 25 years. Based in the Bay Area, Vivek has grown the company globally without venture capital, staying deeply involved in product and running the business as both CEO and de-facto chief product officer.

As QuestionPro crossed $10M then $30M in revenue years ago, private equity firms and acquirers started calling. Vivek chose not to sell and instead kept building. Over the years he has completed about ten small acquisitions and expanded the platform while staying nimble as an independent company.

In this conversation, Vivek explains why having fun, liking your team, and taking some profits along the way makes it possible for founders to play the long game. He also shares how AI is changing market research and why most AI use cases still need experimentation.

Key Takeaways

• Founder Product Ownership – Vivek still acts as chief product officer, believing founders should stay close to the product and customer problems.
• Small Acquisitions Strategy – Rather than selling, QuestionPro grew through about ten small acquisitions that expanded capabilities and distribution.
• Practical AI Adoption – Most AI experimentation fails early, so the team tests many use cases and keeps the ones customers actually adopt.
• Sales Efficiency Gains – AI dramatically improves painful processes like RFP responses and compliance questionnaires that previously took hours.
• Synthetic Research Data – Vivek believes AI-generated personas and synthetic respondents will transform early-stage market research within a few years.

Quote from Vivek Bhaskaran, founder and CEO of QuestionPro

"Two things matter to me that have allowed me to be the founder and CEO for 25 years. Number one, can I wake up every day and have the same level of energy, enthusiasm, and fun? Work and fun, and everything has to be correlated at this point. There is just one life. "Number two is the people around me. I love the team that works with me and hopefully they like working with me too. These are the two things that matter to me: Am I having fun? Am I having fun with the people around me? You got one life, so can you mesh those two things together?

"Ask yourself, am I personally in the game? Do I really want to do this? If those two things are true, then I'd say keep going. How you feel, what you're doing in the morning, how you show up all day, and then who you work with. These are not external. You control both these variables reasonably well."

Links

• Vivek Bhaskaran on LinkedIn
• QuestionPro on LinkedIn
• QuestionPro website

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.

Practical Founders CEO Peer Groups

Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Juan Ignacio Garcia Braschi is a partner at L40, a boutique SaaS M&A advisory firm with offices in Madrid, Lisbon, and Miami. After two decades in banking, private equity, and operating roles, including serving as CFO of ride-hailing company Cabify, he now helps SaaS founders sell companies typically valued between $20M and $200M.

L40 works primarily with B2B SaaS companies doing $5M–$50M ARR, most of them bootstrapped or lightly funded, including companies in Europe and Latin America. Juan explains how today's buyers evaluate SaaS companies, why Rule-of-40 performance still matters even with AI, and how growth rate, retention, and profitability determine valuation ranges of roughly 4–8x ARR.

Key Takeaways

• Growth Drives Valuation: Growth rate correlates most strongly with SaaS multiples. Companies growing 50% command much higher valuations than those growing 20%.
• Rule Of 40 Still Matters: Buyers increasingly expect SaaS companies to combine strong growth with some profitability.
• Financial Buyers Dominant: Private-equity-backed platforms acquiring add-ons are the most active buyers for $50M–$100M SaaS companies today.
• Sell During Momentum: Smaller companies growing 20–40% annually can be an ideal window for acquisition before growth naturally slows.

Quote from Juan Ignacio Garcia Braschi, Managing Director and Partner at L40

"If you think that you're going to sell your SaaS company, you should think of that two years ahead of when you want to sell. So don't wait until you're burned out.

"Keep in mind that you will have to make a profit at some point to sell to serious financial buyers. So when your company is growing at decent 20, 30, 40% year over year rates, that's probably the sweet spot for selling.

"Significant funds have been raised in the past 24 months and that has to be deployed. Traditional private equity firms are more more interested in tech. These days you see more and more traditional private equity firms going into tech and that's increasing competition and driving multiples up."

Links

• Juan Ignacio Garcia Braschi on LinkedIn
• L40 on LinkedIn
• L40 website

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