Executive Assistant to the Founder

Hi there,

Welcome to my annoyingly-long-and-detailed job post.

My name is Travis, and I’m a serial entrepreneur turned investor. I’m the founder of several companies (like Smash Digital, Investing.io, Snowball, etc), and now I mainly invest in small business acquisitions at CapitalPad.

I consider myself a fairly good founder and a fairly good investor, but I’m pretty much useless at a lot of other things. Common stuff like responding to emails on time, ordering contact lenses before I run out, or getting my taxes completed before the very last hour of the very last day.

So cliché, right?

Knowledge is power though, so I’m now attempting to bring an executive assistant to protect me from myself, provide more mental freedom, and lower my cortisol levels. A yin to my yang. A ping to my pong. The peanut butter to my jel… I’ll stop.

I’m looking for a long-term partner to fill an integral role in Travis Inc. Someone who loves organization, information summaries, and figuring out how to do new things.

This role will be working super closely with me personally. Culture and values fit are crucial. Want to see who I am? Here’s my Twitter.

The Role

Looking to work with a hella-proactive EA, who is detail oriented, emotionally intelligent, and digitally native.

I want to work with someone on a long-term basis, integrating you into helping me operate my hectic life.

Requirements:

Personal

• A very high level of emotional intelligence and common sense.

• Empathy. You must be able to see the world from someone else's point of view.

• Positive outlook, and a non-complainer. I don’t vibe with negativity.

Professional

• A friendly conversational writing tone.

• The ability to comfortably speak naturally and conversationally in English.

  • Non-native accents are perfectly fine, but slow verbal communication will not work.

• Extremely detail oriented.

• The ability to micro-manage tasks (as I will not micro-manage you).

• Technically savvy and digitally native.

• A “design eye”. Aesthetics matter in my world.

• Proactive communication. I can be difficult to reach. You have to be the one to get through.

• Proactive task management. You cannot wait for me to tell you what to do. After acclimation, you should be able to proactively work on projects or tasks that need doing, without my instruction.

• Dependable. I need to be able to trust that things are being handled.

• Assertive. I need you to tell me what to do when needed.

Preferred experience

• Obviously as an EA

• Experience with some aspect of digital marketing will make both our lives easier.

• Experience in the finance and investing world would make both our lives easier.

• The last two traits above are not hard requirements, but they will certainly help speed up the ramp up process.

Key Responsibilities

• Inbox management (priority #1)

  • Pre-writing drafts based on expected responses

  • Creating templates in Superhuman (email app) for repetitive responses

  • Curating and organizing non-urgent information for efficient review and response

• Calendar management (not just booking meetings, but actively structuring time)

• Conduct background research on guests for meetings and podcast recordings

• Research and organize due diligence digests on potential investments and deal sponsors

• Draft and edit emails/newsletters

• Edit videos using Descript (training available if needed)

• Build and maintain SOPs to streamline recurring tasks

• Track due dates for staff and investment-related commitments

• Maintain a personalized CRM, tracking key relationships and interactions

• Manage social media DMs, curating and responding as needed

• Handle travel logistics, including flight research, bookings, and on-the-ground arrangements

• Oversee select personal tasks, such as booking appointments and hiring contractors

• Update and maintain some WordPress content as needed

• Support both business and personal matters as needed, with flexibility to adjust focus over time

Why work with me?

• I’m loyal, down-to-earth friendly, will never micro manage you.

• Much of my team has been with me for many years. I treat everyone with respect, and IMHO act fairly in all circumstances.

• I believe that I tend to work on interesting things and speak to interesting people. You would be in this world.

• Longevity in the role.

• The ability to predominantly work on your own schedule.

• Zero babysitting.

• Strong believer that your success is my success.

• Honestly, I think I’m a pretty good dude to work for.

Why not work with me?

(I have character flaws)

• If you need hand-holding. I know I’ve mentioned this several times, but it’s very true.

• If you need someone to motivate you. You must be a self-motivated person, as I trust things are happening in the background without me checking.

• I’m hard to reach. You need to be able to make decisions on your own, or consistently prod me to respond.

• You need to know how to ask the right questions to keep me engaged. “Pie in the sky” ideas don’t flow well with my brain. Tangible “let’s do this specific thing for this specific reason” does.

• You need to be flexible. I can instantly change my mind on something if the facts or my perception of an event changes. This can be jarring if you’ve spent a lot of time and effort on something that we scrap.

If this sounds like your cup of tea, please apply. I’d love to hear from you.