Experience on Both Sides of the Cap Table Spell Success for Extendify’s Founder and Student Investor

Two headshots of men
L to R: Artur Grabowski (CWR '07), Harry Grubman (CWR '22)


The first seven years of Harry Grubman’s (CWR ‘22) life were firmly grounded in New York City where his mother was a journalist, and his father was in business. Life changed dramatically when the family moved to Chennai, India, then Singapore, then Shanghai and finally Mumbai, India. 

Grubman thoroughly enjoyed his family’s globetrotting lifestyle, and when faced with returning to the United States to complete his final years of high school, he admits to being terrified. “I did not want to be the new kid. I was relieved when we moved to Mumbai instead.”

He did return to the United States for college, choosing Case Western Reserve University (CWRU) because of the school’s emphasis on science, technology, engineering, and math. “I wanted to be engaged with STEM because math and science are tools we can use to solve big problems in powerful and tangible ways. Case was always pushing and trying new things, and gave students access to a lot of resources. All of this drew me to the university,” Grubman says.

“It did take a little getting used to. I had never been to the Midwest. Growing up abroad, I had missed out on 11 years of cultural references. What made the transition easier was my roommate, an international student from Beijing, who was going through the same things as me.”


International childhoods, CWRU background create common ground

The first eight years of Artur Grabowski’s (CWR ‘07) life were spent in Poland. His family settled in Cleveland, and he soon developed a love of computer programming. While still in high school, he worked as a software engineer. Grabowski decided to attend CWRU as it offered both business and engineering plus generous academic scholarships.

During college, Grabowski worked for Silicon Valley startup Melodis (now SoundHound) where he stumbled into “growth hacking,” while working on the company’s product.

“I had always worked on the product side of a startup, and this was my first experience with the critical nature of customer acquisition,” he says. “It was quite fun using my creative muscles. It really got the snowball rolling for me to concentrate on business building.”

After graduating from CWRU with a degree in finance, Grabowski pivoted from software startups to a career in investment banking with KeyBank in Cleveland. “I had a lot to learn on the business front and at KeyBank, I got exposure to many different companies and saw how CEOs think and operate. It was like a business bootcamp.”

After three years, Grabowski wanted to get closer to his first love, software. He joined Silicon Valley Bank in corporate development working with established software companies and startups. While there, he made many contacts in venture capital and startup circles. He also set up an investment vehicle for early-stage software startups. 

In 2013, Grabowski headed back to school to earn a Master of Business Administration from the University of Chicago Booth School of Business. During this time, he joined Adobe, a multinational computer software company in San Jose, California, in corporate development. He explains his pivot back to software.

“What people outside the company don’t realize is that Adobe was built on acquisitions and investments. Except for PDF, every major Adobe product was the result of an acquisition. They’d then put products in a suite like the Adobe Creative Suite of Photoshop, Illustrator, InDesign, and other apps. So they valued startups,” Grabowski explains.

“Being in acquisitions and investment for Adobe was a valued position. I met with companies, acquired them and brought them in house. It was a great experience to be on the front end of technology.”

In 2018, Grabowski pivoted personally and professionally. He and his wife had just welcomed their first child and made the decision to return to Cleveland to be closer to family. On the career front, he joined Automattic, a U.S.-based global company most notable for its work with WordPress, a free, open-source content management system for websites. Nearly half of all websites in the world are built with the WordPress platform.

“What was appealing about Automattic is their entire workforce of 700 (now 2,000+) people was distributed which meant I could live and work in Cleveland. I was hired to grow the business both organically and through acquisitions and investments,” he says.

Grabowski had not been on the job long before he realized something was off. “The first two weeks on the job, every employee is required to work in customer support to build empathy for users. What I noticed was a terrible churn rate; many users canceled their subscriptions after a year. People thought it would be easy to build their own WordPress website, got frustrated and gave up. Here was an opportunity to fundamentally change the business.”


Becoming a Founder

A little more than a year after joining Automattic, Grabowski left to launch Extendify with co-founder Chris Lubkert. Their mission was simple: make it easier for small and medium businesses or hosting companies to successfully build digital experiences with WordPress. They also committed to being a distributed company so they could hire the best people who could then work from where they were most comfortable, be it Cleveland, Poland or Pakistan.

Fundraising began in January 2020. “Because of our backgrounds, we had access to investors in Silicon Valley. The early feedback we got was either a good opportunity but not a fit or good opportunity, but the distributed workforce was not a fit. When COVID hit and people were sent home to work, the perception of potential investors flipped. We started bringing on investors, including Village Global and our former employer, Automattic,” Grabowski says. 

Eventually, Grabowski and Lubkert raised a seed round in 2021-2022 that included the chairman of Cloudfest, one of the hosting ecosystem’s most influential events. “That was great validation for what we were building,” Grabowski says.

Prior to the seed fundraising round, Grabowski got a call from Michael Goldberg, executive director of the Veale Institute of Entrepreneurship, who asked if he was interested in adding the CWRU Alumni Venture Fund to Extendify’s cap table. Grabowski thought the offer over carefully.

“At the time, we didn’t have an open round. We were very mindful of the dilutive nature of investment dollars to the founders, which we didn’t want before a future Series A round.  At the time, all of our money was going to product development. We didn’t need the money but knew we could accelerate if we brought in additional funding. I had previously served as a guest lecturer at Case and saw this as a good way to give back to students,” Grabowski explains. 


“I wish they’d had this program when I was a student!”

What’s unique about the CWRU Alumni Venture Fund is that not only does it invest entirely in alumni-led startups, CWRU students are responsible for reviewing deals and running the due diligence process. After an initial screening meeting, Extendify was chosen to advance to due diligence led by one of the Fund’s fellows, Harry Grubman.

Here’s a little back story on Grubman, a double major in computer science and electrical engineering. Early in his college career, he had an aversion to venture capitalists, preferring the problem-solving of entrepreneurs. He had spent years developing his appreciation for startups at the Sears think[box], CWRU’s world-class innovation center, makerspace and entrepreneurship ecosystem. He helped relaunch and led the university’s student entrepreneurship club, ENTP+, for one year. But when Goldberg approached him about becoming a CWRU Alumni Venture Fund fellow, he declined—and then quickly reversed course and accepted.

Grubman explains his pivot. “I realized it was a unique opportunity to sit on the other side of the table. If I were to start a company one day, I needed to know how things worked and understand the decision making that goes on with investing. I’m glad I changed my mind as Artur taught me to view venture capitalists in a different light.”

He adds, “VC relationships are all about building trust and transparency.”

Given Grubman’s background in computer science, one would expect an inherent knowledge of Extendify’s market. Grabowski recognized early in the process that Grubman had no real context of WordPress or its niche ecosystem. During their conversations, Grabowski would coach the student on what to ask about the company. He also asked his investors to guide Grubman and the other students on what to ask and look for when evaluating a company and its founders.

“It was cool to watch Harry’s understanding improve. The more he learned, the better his questions got,” Grabowski says.

From Grubman’s perspective, it was a great learning experience as he came to recognize Extendify’s and its founders’ many strengths. “Being open source, the WordPress ecosystem has a lot of action and little coordination. Successful users are scrappy and can work within the freeform of WordPress, but it’s difficult for hosts. With Extendify, Artur is formalizing efforts in the space by filling in the cracks. His advantage is his intimacy with the WordPress platform and the Extendify solution is scalable and repeatable.”

Grubman and the student due diligence team recommended a $50,000 investment in Extendify. Goldberg and the fund’s other advisors agreed.

Grabowski is grateful for the investment as it helped product development without requiring a massive dilution before a Series A round. He also says the students did a good job leveraging due diligence from Extendify’s lead investors while asking their own questions. He recommends other CWRU alumni to take advantage of the Fund. 

“I’m glad we did it as it gave us the opportunity to engage with the university and students in a unique way. Students get access to real companies and gain real experience. As we scale Extendify, I have access to CWRU talent.”

As for Grubman, the experience gave him an appreciation of funding mechanisms but confirmed he’s not interested in a career in venture capital. A startup may be in his future, but right now, he’s flying high with Boeing after his own due diligence performed during two summer internships with the global company.

Says Grubman, “I’ve loved airplanes for quite a while—probably because of all of the 18-hour plane flights I did as a child to see family. When Boeing offered me a full-time job working on the electronics of their newest aircraft, the 777X, I said yes.”


By Melanie Lux