Matteo Grassi is a five-time founder backed. He grew Popup to over 40 people in the team, and it successfully raised $3.5 million from many backers including Accel, 20VC, and Seedcamp
Unfortunately, the business encountered difficulties and, in January 2024, Popup was shut down.
The episode dives into the challenges Grassi faced in the competitive world of content management systems, the importance of community building, and the crippling reality of venture capital's 'moonshot' expectations.
Now, Matteo works as a mentor and advisor for startups. He also has built an app called Baseline that is designed to help people with bipolar disorder, a condition Matteo himself has, and this venture is being assisted by King’s College London and Bipolar UK. Matteo has a BSc (Hons) in Clinical Psychology from the University of Bologna.
Timestamps:
00:00 Introduction and Guest Background
00:31 The Journey of PopUp
01:40 The Decision to Shut Down
02:58 The Challenges of Building PopUp
10:18 The Fundraising Journey
17:34 Building a Community and Marketing Strategy
24:23 The Downfall and Lessons Learned
30:52 Risk and Conviction in Commerce
32:11 Market Share Analysis: Shopify vs WooCommerce
33:11 The Reality of Entrepreneurship
33:58 The Struggles of Fundraising
38:12 The Impact of Market Shifts on Funding
44:27 The Harsh Reality of Venture Capital
45:46 Advice for SaaS Founders
46:49 New Beginnings: A Mental Health App
51:47 Closing Remarks and Future Plans
💡 Key Highlights
- Why Matteo decided to shut down his business Popup
- The founding story of Popup, what pain point the business aimed to solve, and the challenges of raising venture capital as opposed to bootstrapping
- Why Matteo decided to go into software from e-commerce in the first place
- How Matteo went about raising money and what VCs invested money
- What Matteo would do differently if he went back, such as not doing any community, marketing, or documentaries
- Why Accel dropped Popup eight months before the company shut down
- How Matteo thinks Popup would have survived knowing everything he does now
- Matteo’s insights on Shopify and its presence in the CMS market, partly informed by his former job role working for Shopify
- What happened after Accel dropped Popup, including the challenges faced with an overinflated valuation and a shift in the market
- Whether there was ever any discussion about Popup doing a very large down round, what Matteo did in the last few months before Popup closed, and why he thinks the objective of venture capital is not to make companies successful
- Matteo’s advice to other SaaS founders
- Insights on Matteo’s next business ventures, including advising other startups as a mentor, and with the help of King’s College London and Bipolar UK, working on an app called Baseline to assist people with bipolar disorder
- Insights on Matteo’s book recommendation for SaaS founders, an entrepreneur or leader he admires the most, underrated SaaS tools he uses, the best piece of advice he has ever received, and who Matteo would want as a guest on the SaaS Minds podcast.
-- LINKS --
► Full Transcript: https://nuoptima.com/saas-podcast/popup-matteo-grassi
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LinkedIn: https://www.linkedin.com/in/matteowastaken/
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