No “Line in the Sand”

“Have you drawn a “line in the sand” on when to close your business?”

Line in the sandSmall Business Week is April 30 – May 6.  Intuit’s QuickBooks, a company best known for their accounting software, was interested in hearing takeaways from successful small business professionals. As a QuickBooks user for the last 10 years, I wanted to share my insights.

In April 2016 I was introduced to a business consultant by my CoupleWise co-founder and chief psychologist, Dr. Gary Krane. Dr. Gary had been trying for the seven years before we met to launch a health and wellness software app for couple relationships, with no luck. I took over as CEO in October 2015 with a “no pay, founders equity” deal.

After 3 months of evaluating the opportunity (great), channels to market (huge), and the current product (great concept, poor execution), I concluded the business required a complete overhaul–mountains more than his Board led me to believe. This made Dr. Gary very nervous, which led us to his friend, the consultant.

After a few meetings the consultant asked me, “Have you drawn a “line in the sand” you won’t cross… where you’ll give up and move on?”

I knew why he asked–Dr. Gary and many others went years without turning CoupleWise into a business. Still, his question thoroughly annoyed me!

Drawing a line in the sand to say: “If by X date I don’t achieve Y, I’ll walk away” was unfathomable. Maybe you’re different. More pragmatic. Not me. Fortunately, not my wife, Kim, either. To me, CoupleWise was a mission you ran at with all you heart, mind, and soul. I felt an “anointing” and giving up was not an option. And I did not want folks with a “line in the sand” mentality influencing the company.

Every bit of research I did on the downstream effects of fragmented families stoked my passion to make CoupleWise as ubiquitous as Facebook is for keeping up with friends, or LinkedIn for building business contacts. The annual cost of broken families to US Taxpayers? $165B. The lost productivity and cost to US businesses? $7B annually for 9.6M paid sick days alone, billions more in lost productivity, higher healthcare costs, and more.  Not to mention the growing Corporate Employee Wellness movement, which fits “hand-in-glove” with CoupleWise.

In August 2016, to save resources we moved out of our home and in with family.

Fast forward.

We released our new MVP version November 8th. I stopped efforts to raise seed capital because of Angel investor market sea-changes, and turned my focus to executing my business plan. That month we received a commitment from a UK division of pharma-giant GSK I met while participating as a finalist in the MassChallenge UK business accelerator. This would put CoupleWise in front of 36,000 to 110,000 patients. An important win.

In February, month 16 without pay, we signed a contract with Asirvia (, a new direct sales company, to include CoupleWise in their Asirvia Life bundle of services. They now include CoupleWise in everything they sell.

Our big breakthrough came on March 29th when we signed a contract with ABA 1st Responders Association to add CoupleWise as a benefit service for 1.2 million members.


We leveraged the 1st Responders deal into another contract. We’re now prospecting multiple revenue sources, and a growing pipeline and sales channel. No “lines in the sand”… hard work, a great product, faith in our plan, and unwavering determination. Making CoupleWise a success is more of a 20,000 piece puzzle–not unsolvable, just very challenging.

CoupleWise is the 1st health and wellness application with real therapeutic power wrapped in a beautifully executed, easy, and painless approach for any couple in any stage of their relationship: dating, engaged, living together, married, and even divorced with children. CoupleWise makes growing, repairing, and improving your relationship affordable, accessible, 100% private, 100% confidential. And, the market need is global (click here for most of our research).

Here are my 6 take-aways:

  1. Don’t sell yourself on the business. Dig until you find multiple sustainable markets that need your product.
    1. Build a REAL business plan. Force yourself to think through all aspects of growing your company. Your “game plan” instills confidence.
    2. Build a detailed set of financial projections. Go deep. Get in the weeds. Own the numbers.
    3. Present your plan to industry leaders for feedback. Listen with intent to improve.
  2. Don’t sell yourself on product quality. Test it with real users. Get people to submit evaluation forms. Take suggestions seriously.
  3. Don’t just sell, be an evangelist. Become an expert. Integrate irrefutable data into your pitch. Show your passion to everyone.
  4. Don’t let external circumstances change your internal drive, learn from every encounter. Thank naysayers for their input. Evaluate it for truths you’re blinded to. Be in continuous learning mode. Let new knowledge improve your decisions.
  5. If you are a “line in the sand-er, find out why. Maybe you don’t believe in your business? Fix it. Do you lack requisite skills? Learn them. Is the risk too great? Can you mitigate them. Are you afraid of failing? Get over it. And if you can’t: Maybe you’re not an entrepreneur. It’s no sin, simply know and be who you are.
  6. Bring your spouse/partner into your vision. Allow them to give input. Listen – they know things about you that will help you succeed. They’re a great source of support and encouragement when you experience set-backs. I’m amazed at Kim’s intuitiveness to my needs.

Did Kim & I enjoy cutting everything, including our independence, from our budget? No.  But we work to keep the goal in sight and not allow personal sacrifices to cause us to waver in our determination to make CoupleWise a force for building healthy relationships. Do we succeed at this? Most of the time, but we manage to make progress.

CoupleWise is our 8th startup. I love the journey. It’s real. good. fun. Enjoy it.

Building a business is a long distance race… Don’t do it alone.

Dan Gallo, The Small Business Lifer
CEO & Co-Founder, Relationship 2.0, Inc.


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