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The Winrate Newsletter
Issue 6: Pirates and Romantics
Issue 6: Pirates & Romantics

Hi Everyone, July 23 already! 7 business days left in July. That. was. fast.
My entire month has been focused on the product. It’s been coming along nicely and we are getting close to showtime. Kyle and I were having a conversation about some of the inbound seed and angel interest and it gave me a flashback.
As CRO I would always start planning for the next calendar year in late July, early August. Old habits die hard and hiring is on my mind right now.
York.ie has been incredible as my fractional finance, product, and marketing team, and I feel solid in those areas for the time being. The model is working really well for me. I am still searching for a full time CTO and have a few promising candidates in the mix that I am really excited about! In addition to a CTO I would like to find a couple of dynamic go-to-market types to help me execute on the GTM strategy from sales to onboarding and support.
I have a few people in mind, but joining a 1 person startup with a fractional team is a wild concept for most. Jason Lemkin describes hires at this stage as Pirates & Romantics. Why? Against all odds, startup people run toward the adventure. They seek ownership, impact, and the thrill of building something from nothing. The potential rewards are high but the risks can be too rich for many.
If you or someone you know might be interested just reply to this email or have them send me a DM at [email protected]!
While I am gearing up for a big end of year, I hope you do the same! What are the 1-2 big things that you need to focus on? I’d love to hear from you and offer up support or help if I can.
There are a lot of sellers who read this, so this next one is for you! Sales Advice: Making the most of your H2! Get back to basics and you can close the year stronger than ever.
For many sellers Q3 is a time for prospecting, generating pipeline, and building toward the year end push. Here is what I would do to make these next 6 months some of your best ever.
Focus! Nail the ideal customer profile (ICP,) don't be the rep who "experiments with ICP" during the back half of the year. No matter how good you are, you won't consistently close deals that aren't good fits, follow the data, call the proven fits. Consistency is KEY to hitting quota and finishing out the year strong. Top performers know their zone and they are incredibly intentional with where they spend their time and focus.
Customize. Customization is key. Well researched cold-openers over the phone and Linkedin DM's would be my focus. 100% of the time. Email automation wouldn't be. Top sellers are GREAT at writing, invest in this skill, not just the phone (and vice versa).
Copy. Copy what is working for top performers. Literally copy the way they talk, the questions they ask, and the way they work deals. With 5 months left, I would be in pursuit of “state of the art” technique to win more deals and defeat the competition. Every edge I can get, I am taking! Top performers are always in pursuit of what is working. SO If your team has started to connect with customers over slack or teams, be fast to follow those wins. Disclaimer: Yes I am starting a company following the popularity and success of this new motion. Following the wins let’s top performers stay cutting edge with their technique. When all else is equal in a deal, these moves matter, a lot!
Sweat. Nothing replaces willingness to grind. Both on the job, and in the gym. A fit body is required for a fit mind, this is needed if you are going to push yourself hard enough to make club. Talented hard working peeps often have significant mental health needs due to the tax on their nervous system. Endorphins from exercise help to balance the stress, keep the serotonin flowin, and revenue growing! Top performers in all fields prioritize working out, almost without exception. Don’t wait until January. Treat August 1st like Jan 1st! This will help your end of year performance more than you know!
Rest. Top performers rest and recover like big game cats. You can't be in attack mode 24/7. Some days you need to bask in the sun. Weekends are needed when you are all-in, all week. Most days are INTENSE. Which is exactly why some days aren't. Some days you need to listen to the body and shut it down! Top performers know what go-mode feels like, they know how to push through funk days, they know the difference between being hurt and being injured. When they are injured they are out and they take the rest! I wouldn’t recommend a 5 month sprint. Plan to take some time along the way so you can stay fresh.
Perspective. Marathoners know the pain won't last forever. It's 26.2. Understand WHY you are running the race, WHY you are working so hard, and for HOW LONG. Set a plan and follow it relentlessly. The human body and mind are incredibly strong when given structured goals. Top performers look like super heros, like they can go forever. Inside they are hurting, pushing, remembering why, and using time boxed goals to keep going to the finish! It's intentional!
Go get it!
