A bi-weekly roundup of ways to rethink 2025 November 30 - December 13 (SO SPOOKY) Fresh Starts They Are A Comin' Most people seem to fall into two camps regarding New Years Resolutions They embrace January 1st with SMART goals and hope They actively ignore the New Years Resolution hype and say, "I'm not a resolution kind of person" I'm trying out something new here: I'd like to see YOUR vote in the poll! You'll see the poll results immediately after submitting your answer. Do you tend to set...
14 days ago • 3 min read
More How, Less Hype Hi Reader, If you haven't been living under a rock for the past few years, your inboxes, feeds, and networking events are filled with people breathlessly talking about the potential of AI. Pilots. Proof of concepts. It's all about Potential. Instead of more hype, we're going to show you every place we use AI in our Small Agency Assessment (currently on a Black Friday special), why we're using it, and how we compensate for its shortcomings. 1. Call Analysis We use Fathom...
21 days ago • 2 min read
A bi-weekly roundup of Opportunities November 16 - November 29 Opportunity Knocks for Opportunity Marketing Hi Reader, Let me tell you about Gerald Osprey and his agency, Opportunity Marketing. Gerald started his marketing agency about six years ago after being laid off. For those early years, he tapped his network to do all kinds of work: SEO, content writing, some paid media advising. After the first two years, Gerald was booking about $100K in annual recurring revenue (ARR). In year three,...
28 days ago • 4 min read
A bi-weekly roundup of putting hard-earned dollars to work November 2 - November 15 'Tis the Season for Spending I love Black Friday. It's not just because I'm a business owner, but I consider myself a pretty penurious person and find it difficult to treat myself. It's a constant running joke in my household that I love massages, I can afford massages, but I don't get one unless I've "earned" it in some arcane way, which means I end up getting 1-2 massages a year. Replace "massage" in that...
about 1 month ago • 4 min read
A bi-weekly roundup of mad-->argue-->sad-->move on October 19 - November 1 Talk About Change! I recently delivered a full day training on Change Management and a good third of it was about communication. For those of you unfamiliar with the Kübler-Ross Change Curve, think about the last time that someone broke up with you: first you get emotional, then you rationalize how much better you are off without that person, then you eat a whole pizza and cry a little bit while watching Moana, and...
about 2 months ago • 2 min read
A bi-weekly roundup of AI-enhanced communication tips October 5 - October 18 How AI Podcasts Drive Adoption, Adventure, and Self-Actualization When I conduct a Small Agency Assessment, one of the ways that I help make the recommendations stick is by creating a bespoke podcast using the audio overview feature in NotebookLM, the new hotness coming out of Google. Far too often have I seen a business get really great advice but then don't do much with it, mainly because the advice wasn't easy to...
2 months ago • 4 min read
A bi-weekly roundup of 5-year old learnings September 21 - October 4 I'm A Survivor And Here's How 2024 is a special year: October 10th is Learn to Scale's Five-Year Anniversary. which according to The Knot is...wood? Or silverware? Every October 10th, I produce an Annual Report for Learn to Scale, aka my own performance review. This year's Annual Report is going to be a bit more comprehensive since it's an important milestone. I'm currently deep in the guts of my own history, but in the next...
3 months ago • 4 min read
A bi-weekly roundup of how to focus on just one thing September 7 - September 20 Image courtesy Three Circles Studio Hanging Up My Startup Boston Hat For the past two years, I've been the Everything Else drawer at Startup Boston as Head of Operations and then COO. Many of you that subscribe to this newsletter met me through Startup Boston! As Learn to Scale continues to niche down into the world of marketing agencies, I've stepped away from Startup Boston to better service our current and...
3 months ago • 2 min read
A bi-weekly roundup of refreshing outlooks on common problems August 17 - August 30 Research-Driven Checklists of Perspective, On Sale Now As I mentioned in the last TL;DR, I recently came off a multi-month series of interviews with small marketing agency professionals. I heard all about the problems these small businesses face, from Communication and Culture to Operations and Scaling. TL;DR- the problems that small agencies face are not terribly unique. That being said, the problems small...
4 months ago • 1 min read