Awesome People - Ep 60

executive assistants, task management, delegation

Hi founders and fellow VC Friends!

Each week we deliver one awesome person to your inbox. These are the people you need to know—the marketers, sales gurus, engineers, ops wizzes— who give your startup superpowers 🚀. The best part is, everyone is hireable on a part-time basis.


Please meet Michelle, the Queen of Executive Assistants 👑

Given the insane popularity of this exhausted Friday night tweet, it seems many of you are in the market for an Executive Assistant 😉. We’re here to help. 

Michelle is the founder and CEO of Squared Away, a network of military spouses turned EAs. Military spouses are notoriously on-top of their sh*t given the insane amount of logistics involved in their lifestyles. Michelle’s grown Squared Away from 1 assistant to 160 and in 2019 was Kaneohe Bay Marine Corps Spouse of the Year. A fellow investor and Clubhouse friend, Shane Mac, co-founded Squared Away with Michelle.

Squared Away works with a few of my besties including Cee Cee Shnugg (Boom Capital) and Chaz Flexman (Forward Foods, ex-a16z & ex-Pattern Brands). They’re also trusted by Eniac and Felicis Ventures.

Michelle and her team help founders with everything from fundraising to book launches. You can hire her and her team for project management, chief of staff roles, customer service, social media, etc…the sky's the limit!

Fun fact about Michelle: she hates heights, but loves swimming with sharks 🦈. 

Need help managing tasks, logistics, and your busy lifestyle? Respond to this email and I’ll intro you!


Michelle was gracious enough to share some pro-tips with us 🚀

Delegate your 5-minute tasks

People tend not to delegate things that will “only take 5 minutes.” However, those 5 minute moments add up. An assistant can help you schedule meetings, do research, check and respond to emails, send follow-up notes and project manage. Personally, they can help you schedule appointments, flights, babysitters, grocery delivery, and house cleaning. Find someone to help with all those 5-minute tasks so you can focus on your priorities.

Most people have a hard time delegating because they fall into the “it’ll take me 5 minutes” category or they don’t know where to start. Learn how to delegate. Research and scheduling meetings are two safe places to start. Build trust with your assistant and grow from there. The more you see they are capable, the more you will feel confident handing over to them.

Find someone with your best interests at heart

Working with an EA should feel like working with an actionable partner. They should have your best interests at heart and communicate proactively.

Here’s an example: I had a client who regularly liked to book travel at the very last minute. This led to paying increased prices and being dissatisfied in their seats.

It was a nightmare. I jumped in to fix things.

As soon as I knew he had impending travel, I would make sure to ask his exact plans on his travel day. I had to send a lot of reminder texts to get all the required information. But in the end, my persistence resulted in a smooth travel day and my client getting the best deals.

Tactical tips for you and your EA

Here are a couple of tips for building a strong relationship with your EA:

  • Coordinate weekly calls to set weekly priorities and brainstorm with your assistant (this is a great time to braindump everything that’s in your head).

  • Set up daily recap emails/messages for checking the status of major tasks.

  • Share feedback early and often. Don’t be scared to give feedback to your assistant. Share what works well and areas you would like to see improve. If you aren’t a fan of calls before 10:00 am and your assistant has booked Zoom calls a week out at 9:00 am, share that time isn’t your jam. Feedback is a gift and Squared Away assistants accept this as such.

Looking for an executive assistant? Respond to this email and I’ll connect you! 


As always, let me know if you have any questions and if you want an intro to any of the folks in this email (including the PS section 🎉).

Stay awesome,

Julia Lipton

Founder of Awesome People Talent & Awesome People Ventures (join the syndicate)

If you liked this, ❤️ it below. If someone forwarded this to you, sign up here 💌


Part-Time Opportunities 👀

Fractional Chief Marketing Officer for Insuretech Co - One of my good friends is looking for a fractional CMO who has experience with B2B distribution and in financial services. They’ve raised $3.7M and are ready to 🚀. Ideally, this person has experience launching new products, building a marketing strategy, and can work within a budget. Full disclosure: I’m an angel investor 😀.

Part-Time Clinical Informatics MD for Amibence - Ambience is building a medical AI scribe. I invested via Awesome People Ventures, alongside a16z and Kleiner. It’s the most impressive healthcare and AI/ML company I’ve ever seen. They’re looking for highly driven MDs who thrive in fast-paced, early-stage tech startup environments. This is a rocketship and an incredible opportunity for the right MD. Minimum 4 days a week.

Marketplace consultant for Jammcard - Jammcard is a marketplace for booking top music professionals — you can book remote sessions, lessons, virtual gigs, and more. They’re looking for a marketplace expert who can help drive demand and conversions. You’ll get to work closely with my awesome friend J. Sider who founded BandPage (acquired by Youtube).

If these roles are a fit for you, or anyone you know, let me know and we’ll make the connections!

Most Recent Awesome People 🙏

Katy and Sarah - Design gurus. Katy and Sarah run a design firm focused on healthcare and wellness startups. They were recently featured on Adobe Live and were recommended to Awesome People by the CEO of Webflow.

Rachel - Brand partnerships and campaigns consultant. She’s led campaigns at Uber, Cameo, and Graduate Hotels. Most recently, her work for Cameo drove an additional $200,000+ in GMV over Black Friday + Cyber Monday.

Edem - Video producer and creative strategist. Edem is a top-of-the-line producer trusted by Journey Meditation, Saxx, Footaction, Floodgate, Joinery, and Artemys Foods (Awesome People Ventures port co!).

Want intros to anyone here? Lmk and I’ll connect you!

❤️ ❤️ ❤️