What you’ll learn in this interview:

  1. My 3 hidden gem resources that every business owner and consultant should know
  2. My #1 accounting tool that will outperform your bookkeeper 
  3. The 1 course that helped me refocus my finances without giving up the things I love
  4. The 3 products that I can’t live without (and tell everyone about)
  5. My 3-step, 3-product morning beauty routine that gives my skin an all-day glow 

erin halper interview ladybossblogger

How This Business Owner Helps Women Find Success Beyond The 9-5

Business Lifestyle

1. What do you do? Who do you help?

I run a platform called The Upside, a curated support ecosystem for consultants, contractors and freelancers that provides community, connections and collaboration for growing a successful independent business.

We help women who are looking to grow a rewarding career outside the traditional 9-5, and make meaningful, quality connections with other high-level B2B consultants, spanning all industry verticals, around the country.

Top Resources

2. List your favorite business tools.


  • Criminally Prolific: Dmitry Dragilev generously doles out buckets and buckets of resources and winning email templates that actually work. He’s a true gem.
  • Proposify: Recommended by Upside member Rebecca Orlov, this technology elevates a smaller business into big business status with it’s super professional and seamless proposal templates and backend system, and for a very reasonable fee.
  • SquaredAway: The absolute best resource for finding virtual assistants, perfect for startups, freelancers and consultants needing a little bit of extra support.


  • Dreamers and Doers: Other than The Upside, of course, Dreamers and Doers is one of my favorite communities for supporting my personal and professional growth.
  • Work Bigger: Started by my friend Belma McCaffrey, this curated community is a must for women looking for scaled coaching and a bridge to something bigger in their lives. 
  • Pallas Network: Run by my friend Ann Sublett, this community is a constant inspiration for pushing the status quo through conversation and, of course, laughs driven by Ann’s incredible commentary.


  • Airtable: It’s like Excel, on steroids.


  • Bench: For the price of a traditional bookkeeper, I get more robust reporting and a more streamlined process + a human to talk to if I have questions. It’s a no-brainer.

Erin Halper Interview

3. What is a good course, website or book you would recommend and why?


  • The 30-Day Money Cleanse: I recommend this course for women who want to save towards their goals without giving up the things they love. 
  • How to Have Presence: I love this course because it helped me gain confidence and charisma in conversation, on camera, and speaking in front of a crowd. Plus, Elissa is amazing!
  • The Ooey Gooey: This is an awesome course for developing your leadership skills through strategic storytelling.
  • WTF Am I Doing with My Life?: This course is for anyone who has ever asked herself the question, “WTF Am I Doing With My Life?”, who feels ‘under-fulfilled’, stuck, lost or just straight up knows she can have a more impactful, purposeful and conscious career+life. (Plus, AOC took the first ever version of this course…and look where she is now!)


  • Unleash Your Presence: Upside member Julia Wojnar shares valuable insights and videos on how to build confidence in your communication and speaking. 
  • Kona Kafe: Ko Im’s mindfulness blog helps me remember to be human.
  • Global Sisterhood: This site helps women to find community anywhere in the world and have meaningful, soulful connections.
  • Dannie Fountain: I love Dannie’s relatable and easy-to-digest articles that serve as a valuable resource for women building careers and businesses with joy and confidence. 


  • Her Big Idea: A super motivating and inspirational guidebook that helps women pursue their big ideas, written by my friend and the ever-positive and relatable Haley Hoffman-Smith.
  • Start Before the Product’s Ready: From Upside member Lindsay Tabas, this is the perfect book for budding entrepreneurs looking to align their product/service to their customers and get super clear on next steps and milestones.
  • Susan Groner’s 101 Parenting Tips: Upside member Sue Groner’s easy-to-digest parenting tips are a true blessing for parents trying to juggle it all. When our home lives work well, we can work well and thrive in our careers. 

erin halper interview ladybossblogger

Best Advice

4. What is the best piece of advice you have received?

  • When creating a new business or consultancy, make sure you understand the problem or pain point you’re solving. If you’re not solving a problem or pain point, go back to the planning stage! 
  • Whether you’re full-time or remote, showing facetime and building relationships matter.
  • Pay others to do work that is weighing you down or cannibalizing precious hours that you could be using to build your business or bill clients. 

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5. What advice would you give to other entrepreneurs?

  • Set a deadline of 1-3 years to re-evaluate your business. Don’t give up before that deadline no matter what. Setting a deadline keeps you focused and pushes you forward on hard days when you just want to throw in the towel.
  • Your arsenal of resources and connections are more valuable than any investor or career experience. Keep them close and use them strategically.
  • Find a curated community (co-working space, online community, etc.) that feels like the right fit and maximize that membership to the fullest.

Business Lifestyle

6. What is your beauty and/or fitness routine?



  • Step 1: After washing my face with warm washcloth and water, I splash Loli Beauty Chamomile Lavender Water (we’re talking food-grade beauty!) on an organic cotton pad and swipe all over my face. This takes off any excess dirt without stripping away moisture.
  • Step 2: Then I press two drops of Loli Beauty Plum Oil Elixir into my skin to lock in moisture and create a nice glow for the day. 
  • Step 3: I finish with SuperGoop! face serum for much-needed SPF and to make up for the decades of damage from sporting a deep tan.



  • Long power walks with my friend Valerie who’s still pushing strollers
  • My amazing trainer Bonnie (who still wears a thong bikini at 57 years old) 1x/week. She makes me laugh and gets the time to fly by!
  • Cardiosculpt class 1x/week
  • SLT when I can fit it in
  • Chasing after my two kids… does that count?

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7. List the products or items that are indispensable in your life.

  • High-quality organic cotton sheets from ABC Home that only get softer as you wash them (because sleep is a luxury these days)
  • Comfortable heels from Inez (because I can’t focus on work when my feet hurt!)
  • Thinx period underwear (TMI?)

thinx underwear

Business Models

8. Which female entrepreneur(s) do you look up to and why?

  •  Sarah Blakely of Spanx for her persistence and inspirational positive vibes.
  • Ashlee Margolis Fishman of The A List for her authenticity, sense of humor, generosity of connections and her ability to put herself out there for the benefit of others.
  • Gesche Haas of Dreamers and Doers for creating an ecosystem that is incredibly supportive and authentic in a world that oftentimes feels airbrushed and filtered.

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Stay In Contact

9. List your social media platforms.

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