Erin Halper

Balance is key to productivity and overall satisfaction when running a startup.


Erin Halper is the founder and CEO of The Upside which matches businesses with best-in-class flexible, scalable and on-demand executive talent. Prior to launching The Upside, Erin built a career helping alternative investment companies market and grow their funds, consulting with hedge funds, private equity firms and real estate investors to develop fundraising materials that collectively resulted in more than $3 billion in new funding for her clients.

As Erin’s consulting business grew, she learned that there was an extraordinary amount of talented and experienced executives in her same stage of life who wanted the type of flexible and rewarding career that she enjoyed, but perhaps didn’t know where to start. On the flipside, Erin learned through her clients that there are a significant number of companies that are either overpaying for an outside agency to supplement their business needs or are simply going without, stretching their existing staff too thin. Acknowledging this gap in the market, Erin decided to combine her instinctual matchmaking skills and consulting expertise to help others gain flexibility and independence in their careers, while also helping businesses acquire top talent that can flex and scale with their changing needs. The result is The Upside, a new kind of agency that aims to change the way working works in America.

Where did the idea for The Upside come from?

I was a consultant in the alternative investment space for more than 7 years. I got married and started my family during those consulting years, enjoying all the benefits that came along with being my own boss: flexibility, independence, balance and control of my future. However, I saw so many of my friends either continuing in their full-time positions while struggling to juggle a 50-hour/week job and family responsibilities at home, or drop out of the workforce completely, leaving behind their beloved careers—and income. I found that having only these two choices—working full-time or not at all—was unacceptable, especially for a high-achieving professional who brings so much value to the business world. Having seen first-hand the many benefits my clients gained from hiring me as a consultant vs. a full-time employee, I knew I had to bridge this enormous gap. I created The Upside to match businesses with best-in-class, flexible, scalable and on-demand executive talent, for the benefit of all.

What does your typical day look like and how do you make it productive?

I’ve learned to block out days of the week for visiting businesses, and times of the day for getting hands-on productive work accomplished. On the days that I’m not on-site meeting with potential clients, I start at 8:15am and work through until 5pm, often eating lunch at my desk. However, I give myself a hard stop at 5 to set limits, maximize productivity and avoid burnout. I call it my 5 o’clock work whistle, and have literally ended work-related phone calls simply because it’s 5:00pm. This also is the time that my family knows that I can be 100% present with them with no interruptions or distractions. Balance is key to productivity and overall satisfaction when running a startup.

How do you bring ideas to life?

The first thing I do to bring ideas to life is research. Who else has done this? How have they done it? Have they done it well? Can I do it better? Can I do it differently? Is there room for another player? If I’m still interested in the idea after answering these questions, I’m usually fueled with excitement. I’m an artist and creator by nature so the next step is sketching out the idea, whether that’s a rough logo design, business plan or presentation to flush out the details. I run every idea by those I trust, like my husband who is also a business owner or my first hire who has also been one of my closest friends since high school and former CEO of an Inc. 5000 company. Being able to bounce ideas off of people you admire and trust is invaluable.

What’s one trend that excites you?

Without a doubt the one trend that excites me the most is the movement towards more independent contractors and flexible workers in the workplace. This is happening. In fact, it’s predicted that almost half of the U.S. workforce will be freelance within 10 years. As Millennials come of age in corporate America, they are embracing the technologies that allow us to work from anywhere and the philosophy that work life does not unnecessarily need to cannibalize home life, as it has for so many people over the past several decades. And as rising decision makers, Millennials are embracing the power of creating a talent assortment of full-time, part-time and freelance workers to maximize productivity and their bottom line. It’s brilliant, it’s way overdue and it’s the future of work.

What is one habit of yours that makes you more productive as an entrepreneur?

My husband introduced me to the habit of charging our phones away from the nightstands at least an hour before bedtime, and then not retrieving the phones again until at least an hour after we wake up in the morning. This simple habit has helped us mentally unplug at a time when we are least productive anyway, allows us to maximize our most precious minutes as a family, and enables us to focus better during the daytime when we are meant to be the most productive. Allowing technology, emails, apps, social media, phone calls and texts to ping, buzz and dominate our attention at any given moment, only pulls our brains in a million directions which is undeniably unproductive.

What advice would you give your younger self?

Make as many contacts and connections as possible while you’re working for someone else. You’ll be happy you have them when you decide to launch something on your own. Reputation + connections are the foundation of a successful launch.

Tell us something that’s true that almost nobody agrees with you on.

Millennials are going to save us all. Technically, I’m one of the youngest Gen-Xers, but I truly straddle both generations in different ways. When it comes to the future of work, I’ve always leaned towards the Millennial attitude that work culture as we’ve known it must change and will change as we strive for more diversity, equality and for better work/life balance.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I speak to anyone and everyone who will listen to my story of how and why I started The Upside. Entrepreneurs have a passion that is contagious, making us our own best pitchmen and women. You never know what’s behind the door of any given audience. In fact, The Upside has received some of our most valued clients through referrals from people not even in the workforce.

What is one strategy that has helped you grow your business?

Approaching business development from an angle that maximizes my existing network has served me very well. I’ve found that opening a door from a contact I haven’t seen in ten years is much more fruitful than a cold call or email to someone who doesn’t know me at all, even if it’s a more relevant target client. Nothing is more valuable in business than a good reputation.

What is one failure you had as an entrepreneur, and how did you overcome it?

I started a handbag business in 2005 and took on an equity partner that ultimately didn’t deliver the value he had promised. Partners need to complement each other in skills, resources and values, and in all three categories the partnership failed miserably. I was burned out and broke, but overcame it by focusing on the future of my next career chapter and resolving that I would one day launch another company when the timing was right, and never repeat the same mistake again.

What is one business idea that you’re willing to give away to our readers?

I think there is a huge hole in the market connecting entrepreneurs to press opportunities. There are so many amazing companies out there with visionary founders and brilliant products or services, but no one knows about them because they don’t have a $10,000/month public relations budget or endless hours in the day to pitch editors. I would love to see someone create a technology platform to bridge this gap specifically for startups and entrepreneurs trying to get their stories out. There are similar services that have existed for years, but they do not cater to the unique needs of founders.

What is the best $100 you recently spent? What and why?

The best money spent is money that saves me time. Every week I spend about $100 on Plated, the meal kit delivery service. I’ve been using a combination of these services (Marley Spoon, Hello Fresh, and more recently Daily Harvest) for more than three years. Since we cook dinner at home about five nights per week, meal planning and grocery shopping would significantly eat away at our family weekend time if I didn’t have these delivery services to do the meal planning and shopping for me. This $100 is truly life-enhancing for me as a busy mom, wife and business owner.

What is one piece of software or a web service that helps you be productive? How do you use it?

Google Forms, Sheets and Docs have been exceptionally useful as I collaborate on projects with various consultants and contractors across the country. Not to mention, they are free.

What is the one book that you recommend our community should read and why?

We Should All Be Feminists” by Chimamanda Ngozi Adichie. It’s a tiny book that can be read on a single commute, and should be read by every man and woman, regardless of background. Adichie encourages the reader to open their eyes to what feminism looks like in the 21st century, and open their minds to building more respect and diversity into the fabric of our culture.

What is your favorite quote?

“The secret of my success is that we have gone to exceptional lengths to hire the best people in the world.”
Steve Jobs

What I love about this quote is the phrase “exceptional lengths,” which can mean different things to different people—recruiting in foreign lands, providing out of the ordinary financial incentives, or even providing extensive education and training programs to employees, for example. I always tell our clients that they don’t have to go to “exceptional lengths” to find the best people. If hiring the best people is a priority, as it should be in any great company, then embracing the concept of flexible talent will give them unprecedented access to the brightest, most productive, most loyal and most untapped professional talent pool our country has ever seen.

Key learnings:

• Maximize and exhaust your existing contacts, even if distant, before you spin your wheels cold calling or cold emailing. You may be surprised at the doors they open for you.

• Don’t take on a partner out of exhaustion, desperation or as a last resort. A business partnership is a lot like a marriage. If you have a business idea and need a partner to help execute it, take your time and find someone who shares the same passion and values as you and who can compliment your skills and contacts.

• Do whatever it takes to hire the best people. Period. The best people grow the most successful companies.

• Embrace the concept of hiring flexible, scalable or on-demand talent. Today’s part-time and freelance workforce is one of the fastest-growing, exceptional and, currently, untapped talent pools our country has ever seen.

• Never lose sight of balance in your life, especially as an entrepreneur. There is always more work to do. Setting limits and blocking out time to be productive will help prevent burnout and provide much more overall satisfaction in life and business.


The Upside on Facebook:
The Upside on Instagram:
The Upside on LinkedIn: