Gabe Dalrymple

Opportunity Creation Through Cold Email

I was recently reflecting on the last year, particularly the new skills I’ve picked up, and wanted to touch on one of the more valuable ones – Cold email outreach. Cold email has been one of the most valuable tools I’ve learned, and although I still have a lot to perfect, the deals and relationships I’ve built from sending simple, personal emails to prospects far outweigh the time investment I’ve put in.

I sent my first cold emails when I was 16, way before I knew what the term “cold email” even was. I was sitting in my high school chemistry class, extremely bored as usual, and had been trying to figure out a way to get some sponsors for snowboarding. I’d seen all my friends start to land cool sponsorships with big companies who’d regularly send them free stuff, and I wanted that for myself. I had already landed a sponsorship for Jadyn from GoGoSqueez the previous year, and was motivated to try and get one for myself as well!

Initially, I sent some really long emails, but learned pretty quickly that the shorter ones seemed to get more responses. Those emails went a lot like this:

I sent emails to everyone from small clothing companies to massive brands like Patagonia. After about a month of sending out emails, I began to get some responses. Most were “No”, but after I got my first “Yes”, I was hooked. I got a local clothing company to send me some free t-shirts. Then, Hi-Chew told me that although they weren’t technically sponsoring people, they’d send me a package of free stuff. Finally, I got a response from Jones Soda Co, who would end up being one of my biggest supporters for multiple years!

In 2022, I found myself learning copywriting from Neville Medhora’s Copywriting Course, and was especially interested in trying out cold email. I sent out several dozen emails while improving my copy with each one I sent. I started out very small, sending just one or two emails a day. After just two months of sending emails, I had eight people schedule meetings with me, and gained three new clients as a result!

Here’s some important things I learned:

The shorter the email, the better. My first emails were about 8-10 sentences long, and now they’re usually just three or four.
The subject line “Quick question” beat out everything else in terms of reply rates.
The first line needs to be personal – it’s the first thing they see in an email preview, and differentiating yourself from spam emails is vital.
Ending the email with a single question or action item increases response rates.

After jumping on a sales job in April, my email outreach for my marketing business was put on hold, but that didn’t mean I stopped cold emailing. This email landed me a meeting with a restaurant group’s national marketing director, who I was able to one-call close after scheduling a meeting.

With some time on my hands in between sales jobs, I’m planning on continuing to improve my skillset, and this is one area that I’m looking forward to devoting some more time to.

50 Things I Learned From My First Sales Job

This Monday marked the end of my first sales job as an Account Executive at Atmosphere TV, as I was let go along with basically the rest of the sales floor during a second round of mass layoffs.

The last 8 months has been a big rollercoaster. Cold calling was a very new experience for me, one that took a lot to get comfortable with, but ultimately, I’m grateful to have had the opportunity to start learning sales.

After getting hired in April, I was fortunate enough to start out very strong, closing the most deals in my hire class over our two-month ramp period! Overall, I closed about 110 deals, selling to bars, restaurants, gyms, hotels, and more. I compiled most all of them into a map – Check it out below, or here if you can’t see it:

In August, layoffs took our sales team down from about 175 to about 45, and I was lucky/skilled enough to make it through, which came as a big surprise to me as I watched much more experienced salespeople walk out the door that day by the dozen. December’s round of layoffs took that number to under 10, and with that came the end of my job.

I realize the two most valuable things to come from the last eight months are the work experience and the new relationships, and so, with the free time I’ve had this week, I compiled a list of 50 things I learned, ranging from navigating corporate relationships to closing decision makers.

Starting off strong makes a lasting impression.
Document everything! Conversations, promises, etc.
Competition breeds excellence.
Learning the CRM/software can have great benefits
There’s other ways to get deals besides high volume dialing.
Everyone will always act in their own self-interest
People will act in your favor if your interests are aligned!
Verbal promises of money means no money.
The company doesn’t care about you.
“Trust but verify” means even the small tasks.
Quick deals can be found raiding pipelines of fired employees.
Don’t pitch gatekeepers!
Get to the point with Northeasterners or get hung up on.
“Can you help me with something?” opens doors to decision makers.
Corporate businesses take forever to make decisions.
Don’t call restaurants during lunch!
New businesses are much more accepting to change.
Cold text is a viable strategy for getting to decision makers.
Odds of closing a deal go down immensely after the first “decision” call.
Personal relationships are the easiest deals.
After running a demo and handling objections, assume the close!
Most objections are excuses to get off the phone.
98% of the time, leaving your name and number is pointless.
The less info the gatekeeper has, the better.
Be transparent, but don’t lay out all the cards early in a call.
Silence is a powerful tool in conversation.
Shut up when the decision maker is selling themselves!
Brand recognition builds trust.
Don’t drop the mic early in a call!
The fastest way to a deal is usually a new lead.
Referrals are a great source of warm leads.
You can’t sell a solution until they realize there’s a problem.
Bad calls can throw an entire day off – Take walks to reset!
There are two North American time zones east of Eastern Time!
In mid-market opportunities, setting a demo is often better than shooting for a quick close.
“Champions” can help sell the decision maker, but won’t do all the work.
Commissions are taxed at 25%+!
Selling desperate greatly reduces the odds of closing.
Add value before making an ask.
You can’t lose a deal you don’t have.
Agreeing with a decision maker’s political statements builds trust (I didn’t expect this one to come up as often as it did).
Answer buying questions concisely and directly.
The higher the position (role), the greater the disconnect.
Drinking at lunch kills afternoon productivity.
The best pitches are usually the easiest to understand.
Peers can be better mentors than bosses.
Creativity dies in monotony.
The highest chance of connecting with a decision maker is in the morning.
More connections = More opportunities.
It’s just a job.

As I’m searching for the next opportunity, I look back on my time at Atmosphere with contentment. I got everything I wanted out of the job (except perhaps more money, but I suspect that’ll always be the case), and I can’t wait to see what’s next.

Three things to remember Atmosphere by – My Day 1 Polaroid, a Deal Chain for closing 10+ deals in one week, and a bottle of bourbon for winning a trivia contest!

Mothers Day Love!

Mom continues to be such an objectively amazing person, and words probably can’t even describe the multitudinous ways she’s been an amazing mom. But I guess it’s worth a try.

Mom has an unending amount of love for all of her kids, and that has never been more evident than this last year. Living almost 1000 miles away really makes me appreciate the time we get to spend together in person now. I feel like every hike, lunch, long conversation, and snowboard run with Mom is now twice as special! Thankfully, we’ve always been a family that packs in as much action and adventure as we can to any time frame we’re given, and there has definitely been no shortage of fun times every time we get to hang out!

Just off the top of my head, so many things come to mind when I think of the ways Mom loves me, Isaac, and Jadyn.

She’s been the best educator I’ve had. She’s planned out some absolutely mind-blowing adventures for us when we were traveling around the country. She’s cheered us on at countless snowboard competitions in freezing temperatures. Last year, she literally flew across an ocean with a day’s notice for Isaac. Eternally thankful is a massive understatement for how I feel when I look back at everything she’s done for us!

Okay, so Mom checks all the standard “Loving Mom” boxes, and then some. That’s cool. But what makes her a really unique mom? Well, it would take a while to write it all out, but here’s a couple reasons:

I have yet to meet another person who, like Mom, spends every day surrounded by mountains but still appreciates their beauty as if it were the first time seeing them. Having gone on many hikes with her, I can hardly recall a boring time on the trail. Every hike is appreciated by Mom, and I really admire that.

As of this year, Mom is also my business partner at Breckenridge Marketing! Her eye for design and ability to connect with new prospects and friends have paved the way for a great marketing business! I truly enjoy working with Mom on projects in web design, graphic design, content creation, and more, and our collaborative efforts on a couple recent projects have not only increased my skills in marketing, but allowed us to connect even more through a shared entrepreneurial journey!

Last time I was up in Breck, I had teed up a couple in-person meetings with new potential clients through my cold email campaign I’d been working on, and was able to meet with them in town for some great discussions about how we could help them increase their customer base. It was so great to be able to tag-team business conversations with someone like Mom, and I can confidently say this makes her a pretty unique mom.

One final thing that I have to mention here that I enjoy about Mom is the amazing conversations we have. I really feel like I can talk to Mom about literally anything, and I don’t think that can be said for a lot of sons and their moms. If I had to pick someone to talk to about future aspirations, business strategy, political debate, or just my life in general, she would definitely be in the top two (I realize as I’m writing this that I have those same conversations with Dad too. Guess you’ll have to settle for a first-place tie, Mom).

Those are just a handful of things that I love and admire about Mom. As I mentioned before, words can’t even describe all the ways she is an amazing Mom. But hopefully, that was an acceptable attempt at capturing the gratitude I have for having her in my life! Happy Mother’s Day 2023, Mom!

-Gabe

A Texan in Colorado and a Coloradan in Texas

I’m starting to feel like I’m a local to both Breckenridge and Austin with how much I’ve been back and forth between the two places. I’ve been between Colorado and Texas a lot over the last couple months, and have really gotten to experience the best of both winters – Both the 85 degree “winter” days in Austin as well as the 0-degree, snow-covered climate of Summit County. I finally moved into a new house down here in Austin, which has been really great! It finally cooled off after a long summer full of Texas heat, so I’ve been exercising a lot more during the afternoons!

Fall Travels

After a brief trip to Colorado in early November, I officially started to move into my new house, but didn’t really get moved in until the first week of December. While in Colorado, I was able to get in a day of snowboarding – My first time on the mountain in November in years.

Thanksgiving was spent with the Cortez familia in Dallas, all of us together for Thanksgiving for the first time in forever. Isaac and Jadyn flew down with Mom and Dad, and we had a great week with all the cousins and extended family.

In December, I helped Grandpa Cortez with his end-of-year holiday memorial service at the funeral home. He truly went above and beyond to host an event for all the families who held funerals with Williams Funeral Directors in Dallas this last year, and it turned out great. I filmed and recorded the whole event, and helped with a lot of decorating and setup as well. Grandpa gave some great speeches, and even played the guitar and sang for the congregation. After both services (English and Spanish), we went out for celebratory margaritas.

Holidays in Colorado

I flew up to Breckenridge for Christmas and New Years following my time in Dallas, and jumped right into the winter snowboarding season. It really was a special time all together as a family, and on Christmas, we all got to snowboard together as a family for the first time in a while. It’s rare that all five of us are on the same mountain at the same time, and it had been two years since we had all ridden together!

In early January, our friends the Deweys came up to stay in Summit for a bit, bringing along our friend Morgan as well! We got to board with them a lot, and rode multiple days at Copper and Breck.

Overall, it was a very special time with both friends and family in Colorado. Getting to snowboard with our Texas friends barely ever happens, and we definitely packed it in with a lot of back-to-back days on the mountain.

Since graduating high school, my days on the mountain per season have dropped probably around 70-80%, which I guess was expected. However, that doesn’t stop me from enjoying a couple park days where I can throw a couple tricks and feel like a cool snowboarder again (lol). Park days with Isaac or some friends from Team Summit are some of the best days of the year for me, and I was fortunate enough to get in a couple of those in this season. Isaac and I had a great day in January together at Copper where we got to film a couple cool shots of each other with our GoPros. Check out one of his lines I filmed!

Winter Travels

Looking back at it right now, my fall and start to winter seemed to just fly by. The rest of my winter and start to spring was also crazy eventful, with the Austin freeze (losing power for almost a week!), flying out to New York with Jadyn, lots of tennis and pickleball, snowboard banked slalom competitions, and a ton of work on Gabe Media and Breckenridge Marketing. But those are some stories I’d rather write tomorrow 🙂 Stay tuned for that.