Startup Uncoupling



After three arduous years, DayReel, couldn’t get off the starting blocks -- with many false starts and an unsteady stride, this ‘nearly there’ productivity app ran its course and me, the founder, ragged. What began with a vision filled of excitement and promise became a saga of mistakes, obstacles, and hard fought victories -- a daily grind.

Moving forward with a head full of knowledge, perspective, and a smaller bank account, I’m putting keys-to-page to tell this startup story after taking comfort in similar stories.

Love Struck

Endless days and 10,000 working hours ago, a simple ‘aha’ struck, I needed a better way to manage and schedule my and my family's appointments -- think OpenTable for local services. Seems obvious now, but in late 2013 the local services market wasn’t yet red-hot and was prime for disruption (not disruption as much as innovation), at least from my rose colored glasses and kitchen table in Kansas City, USA.  Following a research deep dive, I discovered a ripe market in the service industry seeking a better way to connect with customers digitally, coupled with an underserved, consumer market frustrated with the tedious mechanics of appointment scheduling. Hmmm.  A multi-billion dollar and growing, service economy and no tailored solution for the household consumer! (Check. Check. Check.) Albeit a monster industry to wade into, I saw low hanging fruit and tailwinds that were going to dramatically shift the market, it was never about if appointment scheduling across vertical businesses was going to happen, it was when.  Buoyed by the opportunity, my personal experience, and expertise, I pursued creating a new platform to revolutionize daily life to address a painpoint all too familiar to me and millions of my household peers.

Like most founders who are solving for a personal need, I envisioned a robust app, fully featured, with beautiful UI design, amazing customer engagement, privacy features, personal referral sharing, third party API integrations, the whole nine yards and the makings of an amazing unicorn marketplace, how hard could this be? Right. 

Boundless Obsession

Thus began a plunge to learn as much as possible about building a Software as a Service (Saas) company. In hindsight, it seems like work but at the time, hours and hours spent reading, researching, and pursuing was pure bliss I enjoyed, and the forward momentum and growth felt exhilarating and significant. Armed with new expertise, the Business Model Canvas, and other valuable industry research and insight, progress was happening but naivete kept me blind to the mountain ahead.

Soon, I realized (not soon enough) that forward progress does not mean traction, even if there’s significant momentum toward getting a viable product built. Strangely, traction in the tech lexicon equates to sales and actual money coming in, unless perhaps you’re a known A-lister in the startup club. Nevertheless, significant progress occurred in bringing DayReel to market with very constrained resources; DayReel / I attracted top-tier experienced mentors, managed numerous offshore development sprints, built a wonky custom web MVP, conducted customer research & market tests, attracted early users, presented as a Rise of the Rest finalist, secured awesome third party partners (that assured a future revenue stream), created a WordPress demo site -- all the while attending events, meetings, classes, weathering rejections, and attempting to rear three teenagers. Unfortunately, this torrent of activity occurred at a snail's pace while the competitive landscape steadily advanced. And still, we needed a working app to attract users to demonstrate traction to the concentrated, few people who wield a disproportionate amount of power and influence regarding capital. 

Cue the Violins

One major miss, I didn’t get others (with technical / startup expertise) inspired by the vision and opportunity who were willing to jump on board (apart from mom friends and personal small business owners). Why? It’s obvious now and to people immersed in the local startup scene but not to a starry eyed novice, it’s RISK st*pid. (although no one actually says stupid). Startups are inherently risky, and talented people prefer/need money, not equity (especially in risk averse areas lacking big financial exits), and they have other interesting options and my “mom app” wasn’t that exciting, and I woefully overlooked the optics. I’m a self-funded, non-technical, middle-aged, female, non-Stanford, first-time founder, who hails from the Midwest, who didn’t have a Linkedin account and couldn’t craft a decent slide deck. While I did possess latent marketing wits, social chutzpah, and expertise of the buy-side of a service industry that accounts for 80% of the U.S. GDP -- it’s still an uphill climb, in altitude, pursuing a tech startup.  So began the chicken and egg dance of team formation and funding, and which comes first. The blogosphere can debate, from my perch it was nearly impossible to get a qualified co-founder without cash and we / I couldn’t get funding sans a technical co-founder.  I encountered plenty of setbacks some self-inflicted, others not, nevertheless, I persisted onward to solve a real everyday problem, and to interject a much needed female perspective into the tech scene.

Last Waltz

After three major setbacks in succession, DayReel ebbed to a logical end this summer; app development was defunded (post beautiful wireframes) as part of a larger company cutback, we were declined acceptance in a leading accelerator program, and the market started to leapfrog DayReel; one of particular appeal, Prefer in NYC from a talented, experienced entrepreneur and VC, Scott Belsky, and naturally, Reserve with Google began making strong strides in the hot local services space. Although these new endeavors feel like personal validation for DayReel, there is certainly disappointment in not being a contributor to a solution.  

Endings are tough. The pursuit of DayReel was costly; personally, emotionally, financially, spiritually, and physically. However, it proved a rich learning experience. Who could imagine a huge ‘oops’ event could boost confidence, but it can.  I’m grateful for the opportunity, along with the privilege of meeting some amazing people, and have a deep appreciation for the encouragement of family, mentors, friends, and best-in-class business partners, Booker and Local Med  -- thank you.


Now, after three months of writing this swan song manifesto, I look forward to closing a few unnecessary assets; GSuite, Heroku, Github, Wordpress, Squarespace, MailChimp, Xero, Slack, Adobe, Invision, Adobe, and AWS --

    AND on to new pursuits and adventures, including marathon training with motivation from an awesome team and a clever, new fitness app, Chorus. Cheers!

In Gratitude to Ben Legg, Riddhiman Das, Marianne Moore, Krista Klaus +

Greg Miller