Authentic &


Matt Douglas, Founder and CEO of Sincere Corporation

Re-visiting My Entrepreneurial Roots

Over the past few months, I’ve been asked several times why I haven’t published any new blog posts. In fact, I’ve only posted two posts this entire calendar year. Well, it’s not just that I’ve been busy with work and life — it’s that I haven’t needed this blog for its original intended purpose. Allow me to explain…

I launched the new blog with some very specific goals:

– Goal #1: Elevate Punchbowl in the minds of large potential strategic partners of our business

– Goal #2: Raise my personal business profile with key decision-makers at these companies

– Goal #3: Spend time to research and evaluate specific vertical industries to help further my understanding of these potential partners (specialty retailers and digital media companies)

As some of you know, in July of 2017, Punchbowl announced a strategic investment from Party City Holdings, Inc. There’s no doubt that this blog had a positive impact on this very important deal. In fact, a few days after I published the in-depth post “How specialty retailers can grow faster using digital platforms” I received an email from the President of Party City Holdings (on a Sunday, no less). In the email, he praised the post, “Interesting Article Matt – Thanks for Sharing – Seems like you’re doing some out of the box thinking….nice to see! I was waiting to see your suggestions for Party City’s Digital solution to increase customer engagement. Maybe we can share points of view soon.” This initial email from him set off a series of meetings that culminated in not only a sizable commercial relationship with Party City but also a $4MM equity investment. Not bad for a single blog post.

Those of you who have followed my entrepreneurial journey over the past decade know that this is not my first blog. I originally started blogging back in 2007 (MyPunchBlog). At the time, I used the blog as personal memoir of the entrepreneurial lessons I had learned along the way. The blog also included a fair number of posts about random things happening in my life (in my defense, the prevailing wisdom at the time is that every startup needs a blog and that it didn’t matter WHAT you blogged about). By 2010, I created much more focused content on my new blog called “StartupSwami.” Over the five (inconsistent) years of that blog, I wrote several posts that were geared toward Entrepreneurs who were just starting out. My target audience was a younger version of myself who didn’t know what Venture Capitalists do or why prioritization is the most important concept in a startup. Some of the posts had thousands of visitors, and several publications syndicated the content with my permission. I enjoyed writing the posts, and it certainly helped to grow my network. However, I also learned that the brand “StartupSwami” was a hindrance — the clever alliteration didn’t come across serious enough to the people I wanted to reach at multi-billion dollar companies.

Armed with this perspective, I launched in late 2015 with the specific goals I outlined above. I wrote several in-depth pieces, aided by folks on my team (thanks Meghan and Stephanie!). Some of these posts took several weeks to research and write and were thousands of words long. In fact, a few of them could probably form the basis for a dissertation on the topic (e.g. the three-part series about the “Past, Present, and Future of the Wedding Industry.”)

Now that I’ve accomplished the original goals I had outlined for, I’ve decided it’s time to re-visit my entrepreneurial roots: I would love for to be a resource for new Entrepreneurs who are starting their journey. When I started Punchbowl, I suffered from a very steep learning curve on many topics. Although there are now several startup resources available (like the fantastic blogs from Mark Suster, Brad Feld, and First Round Capital), I think there is still room for a pure and authentic entrepreneur’s perspective that covers the more tricky subjects of how to start and run a small company. More specifically, here’s what I hope to cover in the coming year:

– Vision & Strategy: How to develop a long-term vision and strategy in the early days (when you barely know what you’re even working on)

– Fund-raising: An Entrepreneur’s view of fundraising through various rounds and how to manage your relationship with VC’s

– Hiring & Firing: What to look for when hiring and lessons I’ve learned about firing employees

– Leading, Managing & Motivating: How to get the most from your team and key individuals

– Persistence & Grit: How to stick with your vision and break-through the noise

– Board & Advisors: What to expect from Board meetings and how to get the most from the people around you

– Marketing & Sales: Where to invest and when to hold back

– Prioritization & Execution: What I’ve learned over the years about how to get shit done

With any luck (and with more consistency) this blog could turn into a valuable resource for Entrepreneurs at various stages of growth. I also hope that the content will help connect me with a new wave of younger folks who may have great business ideas but only a rudimentary understanding about how to really run a business. My plan is to create more “bite-sized” posts that are both easier to read and easier to write (no more epic 2,500 word treatises). Some of the posts will be nostalgic with a lesson learned, and others will be more practical with a step-by-step approach to how I solved a problem. I’ll answer questions that I’m asked, and I’ll try to make my answers not only relevant for the times but also timeless. Every time I write, I’ll be thinking about what I wish I could have read when I started Punchbowl. Whether you’re an entrepreneur or not, I hope you’ll find valuable insights.

So, here we go. If you have entrepreneurial questions you want answered or topics that you want me to cover, leave a comment or reach me by email. Thanks for reading!

©2024 Matt Douglas