Practical Founders Podcast
Greg Head
Subscribe
Tune into the Practical Founders Podcast with host Greg Head for weekly in-depth interviews with founders who have built valuable software companies--without big funding.
Available episodes
Newest first
Oldest first
3 hours ago
#48 – Built, grew, sold, and kept growing a construction software company – Sam Knight
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.
Learn more at practicalfounders.com.
playlist_add
6 days ago
#47 – How to win big when selling your SaaS company for under $50 million – Chris Kern
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?
Learn more at practicalfounders.com.
playlist_add
May 19, 2023
#46 – Founding couple creates valuable company, big exit, and family life too
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.,
playlist_add
May 12, 2023
#45 – Bootstrapped founder still creating big industry impact 30 years in – Dave Savage
Dave Savage was a top-producing mortgage loan officer in the early 1990s who used computers and software to help him sell more. He became a software entrepreneur by creating a new software solution for loan officers to help them educate their clients and sell more. He sold $120,000 of Mortgage Coach on stage at a conference on their first day, which started their 25-year growth journey in the software business.
Mortgage Coach helps loan officers transparently present loan options and educate their clients about the financial impact, which differentiates the loan officer and helps them increase sales and referrals. It started as Windows software then eventually transitioned to the web and mobile devices.. The company grew steadily until the mortgage meltdown in the Great Financial Crisis of 2008-2010 caused its sales to plummet, but it didn’t kill the company. After 2012, they started selling to large lending companies, not just individual loan officers.
Mortgage Coach was a growing and profitable software company with no outside investors when a majority of the company was acquired by private equity investor LLR Partners in 2021. Dave is no longer the CEO of the new company called Trust Engine but he is still is part-owner and an active executive leader helping to grow the impact of the new company.
playlist_add
May 5, 2023
#44 – Helping seniors tell their stories and fight loneliness with easy apps – Beth Sanders
Beth Sanders was selling computer software and equipment for a regional computer retailer in Ohio when she recorded her grandmother’s life stories on a tape recorder. It was so powerful she decided to create a website in 2001 that allowed anyone to journal and share their life stories. Many experiments led to her first paying customer in 2006: a senior care center that wanted to offer life journaling software to their seniors. The LifeBio software business was born.
LifeBio is a leading “agetech” software that uses Reminiscence Therapy Method and storytelling in various media to help older people to capture and share their life stories. LifeBio’s autobiography tools are also used by the Mayo Clinic and other organizations serving Alzheimer’s patients. During the COVID crisis, LifeBio launched MyHello, a new software app that helps seniors fight loneliness.
LifeBio has grown steadily and profitably to over $2 million in revenue with 48 employees, based in a small town near Columbus, Ohio. Mostly self-funded with a little angel funding, LifeBio serves the massive senior care industry in the US with its easy-to-use apps and tools. Their mission is to help people tell their life stories and share them with their own families.
playlist_add
Apr 28, 2023
#43 – A tenacious bootstrapper’s journey to a profitable and sustainable SaaS business
Josh Haynam grew up in the Central Valley of California just 100 miles from the tech center of Silicon Valley--without any awareness of tech jobs or tech businesses when he lived there. He was a successful high school entrepreneur, then supported himself through his college years with his digital SEO agency. Their experiments with custom website quizzes showed promising results, so Josh and his cofounder friends started a company to build the first lead-generation online quizzes as a standalone plugin for websites.
Interact quizzes showed promise with great customer value, but they struggled to sell their new solution to small business owners or marketers who had never seen quiz software before. They experimented, pivoted, and kept going for seven years before they finally reached $1 million ARR with some profits. The ups and downs continued with well-funded competitors, COVID booms and busts, target market pivots, and more.
Interact now is profitable and growing with nearly $3 million in annual recurring revenues, 11 remote employees, and thousands of customers—still without any outside equity funding. Every day, users complete millions of Interact quizzes on their customers’ websites.
Learn more at practicalfounders.com.
playlist_add
Apr 21, 2023
#42: Second-time founder scaling up with product-led growth and 3 employees
Esben Friis-Jensen was a technology professional in Copenhagen, Denmark before he and three Danish friends moved to San Francisco in 2013 to start a new startup called Cobalt. Cobalt.io grew steadily and raised several rounds of VC funding to become a sizable cybersecurity software company in Silicon Valley. Cobalt serves large businesses with a platform and services for larger companies to efficiently test and find security holes in their websites and web applications.
Esben left Cobalt in 2020 to start Userflow to help software companies attract, sell, onboard and support their customers without human touch altogether using a product-led growth approach. Userflow is a no-code onboarding software to easily build in-app explanation guides, checklists, and videos for software product companies to improve free trial conversion and new customer onboarding for expanded retention. Userflow has a free trial and uses its own software to improve conversion and onboard customers without human intervention.
Userflow is profitable and growing with over $3 million in ARR, 600 customers, and just three employees with no outside funding. Esben handles all growth and lives in San Francisco and his cofounder Sebastian builds the product with their UX designer in Denmark, so about $1 million annual recurring revenue per employee.
Learn more at practicalfounders.com.
playlist_add
Apr 14, 2023
#41: A Product Feature Experiment Turns into a Valuable Standalone SaaS Company – Massimo Arrigoni
Massimo Arrigoni grew up in Milan, Italy, and moved to California 27 years ago to create software products and start a family, eventually moving to the San Francisco area in Silicon Valley. While leading product at the software company MailUp, a popular Italian email marketing software, his team built and tested a better visual editor for creating email templates and website landing pages. The free software tool called BEE ("Best Email Editor") became popular and a new product line was born.
BEE end users love the modern and easy-to-use no-code editor which doesn't require email or credit card to use the product for free. The company also sells to SaaS developers who want to embed the BEE builder into their own apps instead of building their own visual editors. BEE is growing with no paid advertising or marketing spend. New users find their free template library and start to use the product instantly with a frictionless experience.
Businesses now pay for the BEE Pro solution making up about half of company revenue and embedded plug-in makes up the rest. BEE is now a standalone company owned by parent Growens with 80 employees and over $10M in revenues. BEE has over 40.000 monthly users and 10,000 paying customers.
Learn more at practicalfounders.com.
playlist_add
Apr 7, 2023
#40: How SaaS Startups Can Grow Sales Successfully With SDRs and BDRs - Christine Rogers
“My B2B SaaS startup needs just more warm leads. But we have struggled when we hire junior salespeople to call on and email cold prospects to generate qualified leads that the CEO or salespeople can close.”
This is a common frustration for startup and early-stage SaaS founders when they hire sales development reps (SDRs) or business development reps (BDRs) to generate qualified leads. There are many misconceptions and pitfalls that make this even more challenging.
Christine Rogers shares her expertise on what is working and not working when hiring SDRs to generate or warm-up leaders in the modern software business. Christine is an experienced SaaS sales leader who has helped develop thousands of SaaS sales and SDR reps to succeed at growing software companies through her company Aspireship.
In this episode, Christine explains:
* What are the different tasks and roles of sales development reps (SDRs) and business development reps (BDRs) in growing SaaS companies
* What tools, processes, and ideal customer definitions are required before you hire your first SDR
* Which SaaS business models make the most sense to use SDRs in the sales process
* Which outbound lead development approaches are productive in generating qualified discussions
* What compensation ranges are typical for SDRs this year
* How to think about SDR business goals and targets
* If you should hire one SDR or a sales manager-doer as your first sale hire
* When should founders hire “full-cycle” salespeople instead of a lead gen-only SDR
Learn more at practicalfounders.com.
playlist_add
Mar 31, 2023
#39: Former VC and funded CEO helps founders grow lasting companies without VC funding – Dave Whorton
Dave Whorton is an experienced tech investor and funded founder who spent the first 20 years of his career at the highest levels of Silicon Valley venture capital and tech-boom startups. He started his career at Hewlett Packard and experienced the famous "HP Way" culture firsthand before he attended the Stanford Graduate School of Business. He joined the preeminent tech venture capital firm Kleiner Perkins and worked directly with John Doerr for several years before launching Good Technology and raising $63 million in venture funding in the early 2000s. He brought in a CEO to run the company before it was sold to Motorola.
Dave joined the large tech private equity firm TPG and directed many investments there before creating his own small venture capital firm and making several investments in the 2000s. Dave started to become disenchanted with the "Get Big Fast" of the venture capital approach. He talked to several founders who were growing businesses without any outside funding and who were building better businesses with better cultures and better outcomes with no intent to ever sell their companies.
In 2013, Dave started the Tugboat Institute, a membership organization that brings together Evergreen® CEOs across industry sectors to share best practices and unique insights, and to develop trusted bonds for their respective Evergreen paths. Evergreen leaders are seasoned entrepreneurs, CEOs, and presidents with the vision, creativity, resourcefulness, patience, and grit to build and scale a business that will stay private indefinitely.
Learn more at practicalfounders.com.
playlist_add
Mar 24, 2023
#38: Spinout SaaS platform for real estate brokerages reaches $50 million – York Baur
Windermere Real Estate is a large and well-known residential real estate broker in the Seattle area. In the late 1990s, they invested to build an internal software system to power their own business and differentiate their services. After using and improving their software for over 10 years, the family owners of Windermere spun out the software as a new company called MoxiWorks. They hired experienced tech entrepreneur and marketer York Baur to lead the new MoxiWorks business as CEO in 2012.
After rewriting the software from scratch, they started selling their solution to other large brokers in the US. They grew steadily and expanded their product platform and their team. MoxiWorks is now a leading platform system for large residential real estate brokerages, serving over 800 brokerages and 400,000 agents nationwide, which account for more than 20% of transactions in the U.S.
MoxiWorks started as an internal technology investment at Windermere Real Estate, but their early growth years were funded by the Windermere owners and customer sales. In 2019, Vector Capital made a major investment to help MoxiWorks expand beyond its current $50 million in revenue and 300 employees.
See the full-text transcript and show notes at practicalfounders.com.
playlist_add
Mar 16, 2023
#37: Bootstrapped for 10 years and sold ProfitWell for $200 million – Patrick Campbell
Patrick Campbell wasn't expecting to be an entrepreneur when he grew up, but after his first few jobs, he struck out on his own in 2012 to create a software company to help SaaS businesses optimize their pricing. Price Intelligently quickly evolved into a tech-enabled service that allowed him to grow, build a team, and ultimately launch ProfitWell.
ProfitWell is a free and powerful SaaS metrics product that automatically calculates MRR, ARR, churn, and other import financial measures for SaaS and subscription companies from their payments data. It is now used by over 35,000 subscription businesses. Profitwell now offers paid products for managing churn, credit card failure, revenue recognition, and price optimization.
Patrick bootstrapped ProfitWell with no outside funding, but they grew fast to 100 employees before being acquired by UK-based Paddle for $200 million in 2022. He openly shares the story of how they started, grew, survived, and eventually sold the company—and how the…
playlist_add
Mar 10, 2023
#36: His first company had big VC funding, but not his second software company – Jon Nordmark
Jon Nordmark founded eBags.com in 1998 as one of the first Internet e-commerce companies and grew it into the largest online retailer of luggage, bags, and travel accessories. Jon was previously a successful corporate executive who led marketing for Samsonite.
eBags raised $30 million of VC funding in 1999 and survived the dot-com boom and the 2001 bust era, but the crazy growth expectations of VC investors often felt misaligned with the profitable growth path of the company and the market. eBags was eventually acquired by Samsonite in 2017 after selling $1.65 billion worth of products.
Jon's second software company is Iterate.ai, a low-code enterprise innovation platform allowing big companies to integrate, test and scale new technologies quickly and efficiently. The company was initially funded by services revenue and then by software sales. Jon eventually raised $3 million in angel funding and a strategic investment from a large customer.
Iterate.ai has grown to over $10 million…
playlist_add
Mar 3, 2023
#35: From website designer to industry SaaS platform to a successful acquisition – Perry Rosenbloom
Perry Rosenbloom moved to Boulder, Colorado in 2011 and started a small business offering digital marketing and custom website services. After building a website for his mother-in-law, an independent therapist, Perry created a scrappy subscription-based website builder platform to make websites for other behavioral health professionals.
The Brighter Vision company grew steadily and efficiently without big outside funding and eventually provided custom mobile-ready websites and marketing tools to over 4,000 therapists.
The company grew to 35 employees with an all-new website-building platform before being acquired by EverCommerce in 2020 for $17.5 million.
playlist_add
Feb 24, 2023
#34: Sold his tech services company to invest in big vision for his BI analytics products – Gopal Krishnamurthy
Gopal Krishnamurthy was an early BI and data analytics expert working for a large company when he left to start a BI consulting company called Visual BI in 2010. Visual BI grew to over 300 employees serving enterprise customers as an evangelist to push emerging Data & Analytics trends with SAP HANA, SAP Lumira, SAP Analytics Cloud, Snowflake, DBT, and Microsoft Power BI. They also created several add-on products, which Gopal and his partner Jay retained when he sold the Visual BI consulting company in 2021 to Atos.
Gopal and Jay now lead the growing team in Lumel, the leading provider of add-on products for the massive Microsoft Power BI ecosystem which was carved out from Visual BI. Lumel gets continuous growth funding with the proceeds of the sale of the services business, but the company is on track to be profitable by end of 2023 with almost 200 employees in the US and India. Lumel products (Inforiver, ValQ, and xViz) gaining momentum and adoption from numerous large enterprises w…
playlist_add
Feb 17, 2023
#33: Bootstrapped a leading CRM for auto dealers that sold for $150 million – Matt Watson
Matt Watson was a two-time software company with two successful exits before he was 40 years old. He started his first company, VinSolutions, in his basement in Kansas City in 2006. VinSolutions started by helping auto dealers upload photos of their cars to sell in the popular Autotrader catalog and website. Matt was the first developer and product visionary who lead a team that build their popular CRM and lead management system to help those dealers manage internet leads and sell cars faster.
Their revenue doubled every year as they grew to eventually serve thousands of auto dealers with their pioneering web-based software.VinSolutions didn’t raise any venture capital or private equity investment as they grew to over 300 employees. In 2011, VinSolutions was acquired by Autotrader.com itself for a reported $150 million.
Matt started Stackify in 2012 as the CEO funding the startup with his own money. Stackify is a tool for software developers using cloud platforms to manage and opti…
playlist_add
Feb 10, 2023
#32: From her kitchen table to global HR employee relations SaaS leader – Deb Muller
Deb Muller was an experienced HR executive at a large global company who left her job to start a consultancy specializing in managing important employee incident investigations. Surprisingly, her customers asked her for a software solution that included her best practices, so she mocked up some screens and had someone build the first version in 2009. She started selling it to fellow HR leaders and her software company HR Acuity was born.
Professional management of employee incident investigations was new when HR Acuity started, but there was no shortage of employee incidents to track, especially in larger companies with more than 1000 employees.
She and her team built a community of HR leaders and led the global discussion about proactive employee relations and transparent HR incident management. Big changes like #MeToo, DE&I awareness, and remote employment during COVID increased the awareness of these HR issues and the tools to manage them.
HR Acuity is now a fast-growing company…
playlist_add
Feb 3, 2023
#31: Bootstrapped to $30 million and still growing their survey tool and research platform - Vivek Bhaskaran
Vivek Bhaskaran was a computer science student in college who worked on an online survey tool for a professor in the marketing department. After school, he built a new survey tool with a fellow software developer while they still held their day jobs. QuestionPro grew slowly and profitably with efficient search engine optimization and viral marketing, avoiding the need to raise any money from outside investors.
QuestionPro grew steadily by expanding the product with more powerful features for larger companies to sell larger deals that required regional enterprise salespeople. They also expanded regionally with offices in US, UK, Germany, Australia, and Latin America. Recently, they have acquired several companies with survey products used by large global companies that added to their customer base.
Vivek talks openly about their key inflection points in their journeys of revenue growth, global expansion, recruiting leadership talent, developing systems and processes, and expanding the…
playlist_add
Jan 27, 2023
#30: Bootstrapped IT mgt. software to over $10 million in annual sales before being acquired - Scott McCausland
Scott McCausland was an experienced software sales leader who decided to go out on his own in 2008 to build a new software business. His technical cofounder built the first version of their new software and Scott started selling it. MVP Systems Software was underway without any outside funding.
They kept adding name-brand customers who used their JAMS workload automation and scheduling software in their IT departments for a variety of scheduling and automation tasks that saved time and money. It was an unsexy but mission-critical software for their users. Their software grew more powerful and useful and they steadily added sales, development, and support staff.
The company grew to over $10 million in annual revenues with 70 employees in 4 global offices before being acquired in 2018 by Fortra (formerly Help Systems. Scott left Fortra in early 2020 and is now working on his next software company.
In this episode, Scott explains:
* Why they sold their product aggressively, but grew…
playlist_add
Jan 20, 2023
#29: Mobile app developer created a software platform to grow faster – Oliver Palmer
Oliver Palmer helped start a mobile app development agency in Sydney, Australia that built simple apps for early mobile phones. When the iPhone launched, Tigerspike grew very fast by creating branded mobile apps for large companies with its high-end design and development services.
Tigerspike also created its own software product—a mobile application development platform with subscription fees—to try to transition into a product-based company to grow faster with VC funding. This was difficult as they prioritized their urgent custom software projects for big clients and chronically underfunded their software product development
Tigerspike eventually raised $11M of outside funding from strategic partners and kept growing. The software platform also grew, but Tigerspike never made the full transition to a product-first software company. They sold the company in 2017 for $85 million. Oliver is open about their vision and their challenges as they grew Tigerspike into a large and succe…
playlist_add
Jan 13, 2023
#28: Bootstrapped B2B SaaS company in India serving IT services companies – Sandeep Kumar
Sandeep Kumar quit his job working for an Indian consulting company to start a software company in 2005 when product-focused startups were not common in India. For the next 10 years, they experimented with product features and customer profiles until they finally found an important buyer with budget power who needed their must-have software.
ProductDossier is now a comprehensive platform for enterprise consulting and IT services companies in India to manage project financials, project resources, and new opportunities in one system. Over 50 large consulting companies in India use ProductDossier to manage their global project portfolios to ensure high-quality and profitable project delivery.
The company has 100 employees and is growing steadily without any outside funding. Sandeep shares the important lessons he learned in his 15-year journey about product-market fit, building trust with big Indian customers, developing a great organization, and thinking big.
In this episode, Sandeep…
playlist_add
Jan 6, 2023
#27: Bootstrapped to over $3M ARR with software for SaaS product managers – Sarah Hum
Sarah Hum studied graphic design at university before she discovered she loved to help software startups create new products. She moved to Silicon Valley to work at Facebook as a product designer, but a side project helped her find a problem she wanted to solve. So she quit her job and built an initial software product called Canny with her technical cofounder while traveling the world together as nomading entrepreneurs. Within a year, Canny created enough revenue for them to live and travel frugally.
Canny is a customer feedback management software for product managers at SaaS companies to collect useful product feedback inside their products, then prioritize requests and communicate with customers about their requested features. The Canny product has evolved quickly using its own product to engage with customers and make decisions about the next product features and improvements.
Canny is growing steadily with over $3 million in annual recurring revenue and 13 remote employees. The…
playlist_add
Dec 30, 2022
#26: His SaaS business is scaling fast by helping other businesses to grow – Mark Abbott
Mark Abbott was an active investor and board member for 20 years when he realized that most of the 100+ companies he helped were not good a their “business fundamentals.” The fundamentals of setting long-term goals, making short-term plans, and then aligning teams and individuals to make efficient progress. He thought of writing a book but discovered the book “Traction” by Gino Wickman and his branded EOS® (Entrepreneurial Operating System) system.
Mark worked with his cofounders in 2016 to create a software platform that aligned with the principles and processes of EOS and other “Business Operating Systems.” Soon Ninety.io (now just Ninety) was a popular software used by EOS coaches and business consultants. They licensed the branded terminology from EOS Worldwide, which presented both opportunities and challenges.
The company grew steadily, funded by revenues until Ninety had over a thousand customers and more than 50 employees. In 2021, Mark talked to just one tier 1…
playlist_add
Dec 16, 2022
#25: Bootstrapped a global SaaS business in Scotland for a “massive niche” market
Craig Letton quit his corporate sales job in 2011 to take over his parents’ small printing business in Scotland. It was his first time running a business and he learned hard business lessons quickly. Eventually, he discovered a huge need for custom-printed promotional materials by frontline salespeople in the global drinks and beverage industry. He sold their printing equipment to focus just on the software to solve this tricky problem for those salespeople, marketing departments, and regional printers.
Running the business for revenue and profit with no outside funding, Craig grew the MRM Global business slowly with big brands in the alcoholic beverage industry all over Europe. They worked hard and stayed frugal and started to grow. Then COVID hit and revenues evaporated. Their survival tactics helped them keep going and even grow faster when restrictions were lifted. They raised some practical funding from BGF Capital in the UK to stay alive during COVID lockdowns and expand quick…
playlist_add
Dec 9, 2022
#24: Bootstrapped event registration platform for triathlons and running races – Jeff Matlow
Jeff Matlow is a serial entrepreneur and a crazy triathlete and a long-distance runner who found a way to put those passions together in a software startup that grew up fast. He saw an opportunity to create a better registration experience for endurance events like 5Ks, marathons, and triathlons.
In 2008, he sold the big deal to USA Triathlon and set out to build the website and registration platform he envisioned. The company I Am Athlete (now called imATHLETE) went live with their platform and started selling to hundreds, then thousands, of other endurance event managers all over the US. The company grew without big funding and the solution expanded to manage payments, social media promotion, and more.
In 2019 Jeff sold the company to a major endurance event company. Jeff shares the challenges in growing this company and the learnings from trying to grow with a strategic partnership. Like running a marathon or climbing Everest, the journey is hard and how you approach every day is…
playlist_add
Dec 2, 2022
#23: Creating massive impact with a specialized school fundraising platform – Howard Gottlieb
Howard Gottlieb created and sold several businesses before starting a school fundraising website in 2003 called Easy Fundraising Ideas. It grew into the most popular Internet website for school fundraisers. He experimented with many business models and ideas while the fundraising industry still wasn’t changing or growing.
In 2012, Howard started Read-a-Thon as a literacy-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.
Their relentless focus on elementary school fundraising and their culture of continuous improvement helped them grow faster and create a much bigger impact. In 2022, Read-a-Thon helped thousands of schools and students to raise over $30 million in donations. Their platform has tracked over 30 billion reading minutes by students who have used the platform to earn donations.…
playlist_add
Nov 25, 2022
#22: Grew a niche vertical startup into a global industry leader – Scott Pickard
Scott Pickard didn’t know he was embarking on a 15-year software entrepreneurial journey when he signed on to manage a horse veterinary practice in Calgary, Canada. But they had built some internal software to help them manage their large practice that drastically improved their business results. Soon other horse vets wanted their HVMS software and the Business Infusions software business was created with Scott leading the small team.
Business Infusions grew steadily without big budgets, big funding, or a big team since 2006. Equine (horse) veterinary and hospital practices all over the world heard about their software and lined up to buy it. Now Business Infusions powers over 400 sizable veterinary practices all over the world. The company was acquired for cash by Merit Holdings in 2021 to run as a standalone company to expand its solutions to continue serving its clients.
Scott and his dedicated team weren’t in a glamorous industry with fancy modern technology, SaaS best practi…
playlist_add
Nov 18, 2022
#21: Bootstrapped in Australia then moved to the US to grow much bigger – Josh Cameron
Josh Cameron and three university friends started a scrappy software company in Brisbane Australia just after graduating. They had run the popular college bar where they discovered there was no simple software solution to track, onboard, and schedule hourly employees. They started Tanda in 2012 and it grew into a successful workforce management software company in Australia —without any outside funding.
The four founders moved to Chicago in 2019 to expand their North American business. Their product worked fine in the US, but sales, marketing, and operations all had to be rebuilt, which took years to figure out. They acquired the Workforce company and took on that brand and domain name outside of Australia.
Now Workforce.com is a leading workforce management software company that helps improve time and labor management for shift and hourly workforces. Their 130 employees serve 6,000 customers in 80 countries with employee scheduling, time and attendance, employee engagement, analyt…
playlist_add
Nov 11, 2022
#20: Grew on-demand marketplace out of a search marketing agency – Joe Griffin
Joe Griffin recently left his job of 8 years as co-CEO of ClearVoice, a company that he and co-founder Jay Swanson started in 2014 out of their digital marketing agency business in Phoenix, Arizona. ClearVoice was acquired by Fiverr in 2019 and has been operating as an independent subsidiary since then. Fiverr is now a large public company with a global reach.
ClearVoice was created in the fast-changing web search marketing industry in 2014 out of the need from larger companies for high-quality content to drive their organic website traffic. Joe and Jay previously ran their search marketing agency iAcquire and used profits to self-fund the first ClearVoice platform. They eventually raised a small amount of practical outside funding, including a seed funding round of $1.5M and venture debt of $2M.
ClearVoice is now a leading platform for brands to hire industry-savvy experts to write useful content that is branded for their communities and customers. Thousands of brands and over 10,00…
playlist_add
Oct 28, 2022
#19: Practical VC seed investor explains the institutional funding game – John Francis
John Francis is a general partner at Stout Street Capital, a venture capital fund based in Denver, Colorado. Stout Street has made 70 small seed and pre-seed investments in software startups outside the big tech centers in North America.
Unlike big Silicon Valley VCs, almost half of Stout Street's investments are in practical startups that have reasonable valuations, sustainable growth models, and won’t need more outside investment before they exit.
In this in-depth interview with a “practical funder,” John explains the ROI math of professional venture investors and reveals how they think about investing. John also has great insights on how founders should think about raising money, or not, in the first place.
In this episode, John explains:
* The basic investment math that a seed-stage venture fund manager needs to deliver the expected return to their “limited partner” investors
* What kind of investment valuation and eventual exit outcomes are required to raise inst…
playlist_add
Oct 21, 2022
#18: Bootstrapped a podcast recording platform to scale in Silicon Valley - Zach Moreno
Zach Moreno was a full-stack developer and coding instructor in Northern California in 2015 when he discovered audio podcasts. There wasn't a remote podcast software for recording high-quality audio over the Internet, so he decided to create one. He and his childhood friend Rock Felder started working on their product and startup idea while they still had full-time jobs, with Zach as the CEO and CTO.
Now Squadcast is one of the leading podcast recording studio platforms used by tens of thousands of audio podcasters all over the world, including me. Squadcast has since added high-quality video recording for YouTubers and other creators to easily generate professional-quality video content without using a professional studio.
With 15 employees and over 10,000 customers, Squadcast is growing steadily and scaling up, but they are still a bootstrapped company with no outside investors. This is unusual in such a fast-growing market like podcasting tools and also because the co-founders liv…
playlist_add
Oct 14, 2022
#17: Creatively grew and sold a threat intelligence product with practical funding - Karl Swannie
Karl Swannie was a geographer working in the scenic city of Victoria, British Columbia, Canada, when he started analyzing social media data based on location. He quickly saw there was valuable real-time information that was not being used, so he started Echosec Systems to find a practical use for those insights.
After several years of experiments and hard startup lessons learned, Echosec finally shifted from being an inexpensive news/insights tool to a comprehensive threat intelligence platform for large organizations.
Echosec Systems is now a leading open-source intelligence service (OSINT) that uses publicly available information (PAI) from social media and other sources. They help public and private organizations improve situational awareness and identify threats using geographic insights with real-time data.
Echosec was partially sold to a "search fund" called The Tusker Fund in 2020 and Jeff Oldenburg came in as CEO to scale the company, which he did. In 2022, Flashpoint acquir…
playlist_add
Oct 7, 2022
#16: Growing from scrappy startup founder to scaling-up SaaS CEO - Brad Redding
Brad Redding calls his first startup a "successful failure." It didn't end well, but he learned several very important lessons that helped him be more successful with his second startup, Elevar. Now the bootstrapped SaaS company is growing steadily with 45 remote employees. And Brad is learning fast to be a capable CEO of a larger SaaS software company.
Brad's deep experience with e-commerce advertising data and conversation tracking analytics helped him find a problem to solve. He and his cofounder funded the development of the first product by providing consulting services to the same customers they were trying to serve with their new software product.
It took three years before they found product-market fit and started to grow steadily and profitably. Now Elevar is a growing SaaS business that helps 6,500 e-commerce and direct-to-consumer brands that use Shopify to ensure the accuracy of their conversion tracking data and analytics. Brad has never raised outside funding and he has…
playlist_add
Sep 30, 2022
#15: Scrappy startup founder changes the way cars are bought online - Daniel Yuabov
Daniel Yuabov was a 22-year-old IT manager in New York who wanted to buy a new car. He was so frustrated with the buying experience that he started a software company called Carvoy to make it easy for car buyers to find, buy, and finance a new car online. He grew the company for 5 years—without VC funding—and sold it to a giant Fortune 500 company in 2020.
Daniel quit his job in 2015 to build Carvoy's first product using developers in Ukraine. It allowed consumers to choose a new car online and then buy it easily from a dealer. Their first version was interesting to consumers but resisted by most car dealers. Their second solution had them manually arranging the car purchases behind the scenes for their growing crowd of online buyers.
It wasn't until they started automating every step in the car buying process, including choosing a car, getting a confirmed best price from dealers, pre-approved lending, and delivery that they started to sell thousands of cars. They pivoted from a…
playlist_add
Sep 23, 2022
#14: Created her second software company around her world-traveling life - Melissa Kwan
Melissa Kwan created her first software company in 2014 and then sold it in 2019. It was extremely difficult to start and even harder to grow, but it's how she learned what not to do in her next startup and what was really "non-negotiable" in her life. Now she's a nomadic world traveler and the founder of a growing software business.
Melissa started Spacio to provide a technology solution to high-end residential real estate agents to capture visitor names electronically at open houses. It took years to find the right features that someone would pay for while tapping out her savings--and her family support. She sold the business in frustration to find a better business idea and to stop sacrificing everything for her business.
Melissa started her second software business, eWebinar, to solve a painful problem she faced while selling and supporting software. eWebinar is an automated webinar platform that provides interactivity and real-time chat support for software companies. Her busine…
playlist_add
Sep 16, 2022
#13: Founder with 2 exits shares how he achieved real product-market fit twice - Seth Radman
Seth Radman created, grew, and sold two music app startups in his twenties. A saxophone player in his college marching band, Seth was passionate about helping musicians and school band directors to improve how they learn music using technology.
Seth was the founder and CEO of Crescendo, an interactive music trainer that provides real-time performance assessment feedback using acoustic pitch detection and machine learning as a mobile app. With a little angel funding, Crescendo grew to over 1M users and 7,000 schools before being acquired by Ultimate Guitar in 2018.
He was also co-founder and CEO of Upbeat, a bootstrapped startup providing a virtual music collaboration platform for school music departments. When schools shut down during COVID, Upbeat allowed musicians to rehearse and perform music virtually with others in real-time without sound delays. Upbeat grew to over 200,000 users in 12 months and was purchased by 5,000 schools before being acquired in 2021 by MakeMusic.
"Having…
playlist_add
Sep 9, 2022
#12: Practical investor provides savvy help for vertical SaaS founders – Dougal Cameron
Dougal Cameron created Golden Section to provide support and practical funding to SaaS founders with deep experience in select vertical markets. Their founder-first approach is different than the traditional VC or private equity investment model which often doesn't work out well for founders in the end.
Dougal's family had been investing in software companies for over 20 years through their Houston-based family office. Now Golden Section includes a founders studio for venture development, a world-class software product development service, and optional equity funding for B2B SaaS founders with deep domain experience in their industries.
This is an example of one of many possible ways that funding can be practical and helpful for founders who want to accelerate growth but don't want to play the unicorn-hunting grow-or-die game required by most venture capital investors.
"Our capital needs to look very different than the traditional venture capital side, where 66% of the time venture-…
playlist_add
Sep 2, 2022
#11 - Bootstrapped to exit in 6 years against funded competitors - Sean Meister
Sean Meister was a sales professional and leader with a successful career selling hospital and medical supplies before he left to join his long-time friend who had a vision for a new software company serving smaller trucking fleets with simple GPS-tracking fleet management software.
Sean was a co-founder and COO of M2M in Motion, a self-funded software company based in the Chicago area. Sean wasn't the trucking industry expert, the crazy entrepreneur, or the visionary salesperson. He provided the savvy help to get the company started and the operational leadership to build a scalable sales team, reliable product development, and quality customer operations.
M2M in Motion was bootstrapped with founder funding, then customer funding (revenue), to grow to over $5M in revenues before being acquired in 2021 by a larger vehicle telematics company, AAMP Global. M2M in Motion allowed small and mid-sized fleets to track their vehicles with a simple software solution and GPS-tracking devices.…
playlist_add
Aug 26, 2022
#10: From scrappy software entrepreneur to savvy SaaS CEO - Thomas Brown
Thomas Brown creatively bootstrapped his software company and ran it as a very small "lifestyle" business before committing to growing his SaaS business with a larger team.
Thomas was an independent insurance claims adjuster in the 1990s in New Orleans, Louisiana before quitting his job to start one of the first insurance claims management software companies called ClickClaims. It grew slowly and profitably as a very small company for over 10 years before Thomas sought help from advisors to see how he could grow to the next level and learn to be a real CEO of a bigger SaaS company.
E-Claim is now a steadily growing vertical SaaS business with 18 employees and over $4 million in ARR. They have helped independent insurance adjusters and insurance carriers process over 2 million claims with their ClickClaims product since he started the company in 1999.
"I know this sounds cliche, but I didn't get into this for the money. I got into it because I'm a guy from South Louisiana who's been…
playlist_add
Aug 19, 2022
#9: Bootstrapper gets practical funding before getting acquired for $22 million - Nick Santora
Nick Santora bootstrapped Curricula for 4 years with his co-founders before raising $3M in practical funding and then getting acquired in 2022 for $22 million.
Nick and his co-founders quit their jobs to build innovative story-based education courses and a single-purpose learning platform for cybersecurity security awareness training. Nick had found a big hole in the cybersecurity market while working as a cybersecurity trainer in the electric utility industry.
Curricula features fun and engaging training content, which was the opposite of the typical "death by Powerpoint" training that users ignored. Now Curricula is a powerful platform that allows companies to create their own engaging content and then measure custom training results.
When they almost ran out of cash before revenues grew, Nick says. "I would do anything I could do to keep this heartbeat going instead of getting an investor to run our future. Once that starts happening, I knew it was going to start cascading into d…
playlist_add
Aug 12, 2022
#8: Bootstrapped to $100M exit with just one employee - Jeremy Clarke
Jeremy Clarke created, grew, and sold his software company in a most unusual and successful way:
He grew WebMerge to $4M revenue by just himself in 6 years before hiring his first and only employee, a strategic sales rep. It's an incredible "bootstrapped unicorn" success story that ultimately was worth $100M when he sold WebMerge in 2019.
WebMerge was an online service that automates document creation to automatically fill in any documents with merged data from any source. WebMerge automatically generates PDF and Microsoft Word documents. Think of it as "mail merge for the web."
Jeremy's first employer, Formstack, ultimately acquired WebMerge to bring Jeremy back to the Formstack team and renamed the product to Formstack Documents.
In this episode, Jeremy explains:
* How he came up with the idea and pitched it to his employer before building it on his own
* How he grew revenues to $1M ARR before he quit his day job as a full-time software programmer
* What it was like to gro…
playlist_add
Aug 5, 2022
#7: From consulting biz to serious SaaS exit in Silicon Valley - Luke Hohmann
Luke Hohmann was an engineering and product management leader at Silicon Valley startups before he became an acclaimed author and speaker in the enterprise software development world. He used funding from his consulting business—plus revenue from his first big customers—to build a new software product called Conteneo.
Conteneo was enterprise collaboration software that enabled the biggest companies to engage their leaders in new ways to make much better decisions about product portfolio investments. Started in 2010, this idea came out of several of the gamified collaboration exercises Luke used in his consulting business. Conteneo software customers include Adobe Systems, Cisco, Emerson, HP, Rackspace, and Reed Elsevier.
As the Conteneo software business grew, their consulting business shrank. Eventually, Conteneo was acquired by a strategic partner who was also a leader in enterprise software development and innovation, Scaled Agile. Conteneo was rebranded as SAFe Collaborate.…
playlist_add
Jul 29, 2022
#6: Self-funded 3rd venture to a big exit in 18 months - Steve Gelley
Steve Gelley created two successful businesses and learned important lessons before he and a cofounder self-funded a third startup that was acquired in only 18 months for a big prize.
Steve started his entrepreneurial journey by buying, improving, and then selling CPA accounting services firms in the Eastern U.S. Then he grew his first VC-funded tech startup, Xendoo, to innovate in the small business accounting services space.
He exited Xendoo and worked with a partner to fund and create a new startup called wemlo to automate the manual process of processing mortgage loans for mortgage brokers. Only 18 months from starting, including four strategic pivots, Steve and his cofounder, David Rogove, sold wemlo to a strategic buyer owned by RE/MAX.
Steve says, "Nobody tells you that founders end up spending so much time on funding and the optics of the dog and pony show that no one's running the business. It's actually counterproductive."
In this episode, Steve explains:
* Why he sold…
playlist_add
Jul 22, 2022
#5: Lessons and successes building products for developers – Hamid Shojaee of Axosoft
Hamid Shojaee is a technical founder and serial entrepreneur who created several software companies and dozens of products in the last 25 years. He sold his two software companies in 2021—Axosoft and Pure Chat—and now is an active investor and has a new startup to keep him busy.
Axosoft was popular project management and bug-tracking software for developers that he bootstrapped to launch in 2002. It grew profitably for years until it met stiff competition despite active efforts to grow. Dozens of product experiments finally produced a hit, the popular software GitKraken.
In this episode, Hamid shares some hard lessons learned:
* How he and his team experimented to test new product ideas and don’t invest until they prove real user traction (DAUs)
* The challenges of raising money from investors who want faster revenue traction too early in the product-led growth cycle
* The challenges of not being the dominant leader in your market in the long-run
* Selling one business…
playlist_add
Jul 15, 2022
#4: Winning the vertical software game with steady growth - Dan Jaffe of LawLytics
Dan Jaffe is the founder and CEO of LawLytics, a popular website marketing platform for small law firms. Dan was a practicing lawyer before he became an internet entrepreneur with his first venture, which he sold before he started LawLytics in 2012. LawLytics was acquired by the Australia-based Smokeball-LEAP-InfoTrack Group in 2021. Dan is still growing LawLytics as its leader of the acquired company.
LawLytics is a website platform for small law firms who want a successful website but don’t want to overpay an agency or struggle with software that isn’t built for them. LawLytics has templates, designs, and lead-generation tools specifically designed for lawyers to generate business efficiently.
In this episode, you’ll hear how Dan:
* Transitioned from being a practicing trial attorney to an internet entrepreneur and SaaS founder
* Created and sold his first business, an online law firm directory
* Self-funded LawLytics then added small investments from angels and a loca…
playlist_add
Jul 8, 2022
#3: From bootstrapped add-on to white label success - Rafael Zimberoff of ShipRush
Rafael Zimberoff was CEO of ShipRush, a software company he founded in 2001, then grew, and eventually sold in 2017 to Descartes Systems Group for $17 million. Rafael started ShipRush as an add-on product for popular CRM and accounting software and was a pioneer in shipping technology for small businesses.
ShipRush is now a comprehensive shipping platform for small ecommerce providers so they can easily process shipment orders and carrier labels for USPS, Fedex, and UPS. ShipRush integrates with popular ecommerce and accounting platforms, including Shopify, Amazon, eBay, Quickbooks, and more.
In this episode, you'll hear how Rafael:
* Boostrapped his tech services company to fund their first software product then grew without outside investors
* Created a popular add-on software product for bigger software ecosystems as an efficient way to find customers and grow revenues quickly
* Managed complexities of being an early pioneer in shipping technology working with large carrier…
playlist_add
Jun 26, 2022
#2: Bootstrapped to $2 billion valuation in 10 years - Jonathan Cronstedt of Kajabi
Jonathan Cronstedt, also known as JCron, was the president of Kajabi software from 2016 through 2021 as he helped the company grow past the early startup years. JCron is a savvy entrepreneur, digital marketer, and sales leader who shares the story of the bootstrap founding of Kajabi through getting $550M in venture capital funding in 2021.
Kajabi is a leading "knowledge commerce" platform for experts and entrepreneurs to market and sell their expertise as online content. Started in 2010 to help early internet marketers and small business experts deliver videos and training, Kajabi has helped over 30,000 creators to sell their expertise and expand their businesses.
In this episode, you'll hear how Kajabi:
* Had $1M+ annual recurring revenue the moment the product launched after coding on nights and weekends for a year to create the first product
* Founder and CEO Kenny Rueter grew revenues ahead of expenses to stay profitable from day 1 to over $50M in revenue 10 years later
*…
playlist_add
Jun 19, 2022
#1: Self-funded spinoff to software growth powerhouse - Todd Watson of Showit
Todd Watson is the owner and CEO of Showit, a popular no-code website builder and platform for designers and photographers. Todd is a native of Phoenix, Arizona where he started as a videographer before joining a friend in 2006 to create a scrappy software business that made inexpensive photo-presenting and sharing tools for photographers.
The Showit company was created when Todd took one of their two products and half the small team in 2010 to spin off Showit as an independent business. The small revenue from the small customer base and his own savings allowed them to rewrite Showit for the cloud and then continue their fanatic customer focus to keep growing every year.
Now Showit is used by 35,000 designers, photographers, and small businesses as their website platform using its elegant “Photoshop-like” no-code visual builder. The Showit company is growing quickly every year and is profitable, yet Todd has no interest in taking outside funding or selling his beloved company.
I…
playlist_add