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A completely Un-Researched Personal Perspective on Overcoming the Trough of Sorrow

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In business, as in life, there are ups and downs, and oftentimes they come out of nowhere and blindside you, instilling doubt or confusion where there used to be certainty. In the startup world this is called the Trough of Sorrow- a period of time in which the founders lose their way while seeking product market fit. While the term originated in tech, it applies to startups across industries, and most certainly has applied in my journey founding Swig + Swallow.

 

In my experience founding Swig + Swallow, getting in and out of the Trough has been 100% psychological. What I’m about to say may sound counterintuitive, but I believe there’s always a way to manage real constraints. Don’t have enough product? You can make more or run out for a while. Need content, but don’t have a content team? Learn how to make it yourself. Need to fulfill a big order but don’t have the money to do so? Get PO financing, take on a loan, take on investment, etc. Of course there are unpredictable situations that can sideline or bankrupt a business, but the overwhelming issues faced on a day to day- at least with our business- have been manageable with some (sometimes a lot of) creativity.

 

When there are clear constraints, it’s easier to see clear steps forward.

 

The worst Trough of Sorrow moments for me have been when everything about the business seems “normal." Maybe you had an off day, week, or month, but there are no critical differences in the business. One day you wake up, and for some reason, you just feel different. Yesterday you were killing it, running at a million miles an hour, rainbows followed you everywhere, and the favor of the gods shone upon you. Today you wake up and objectively, little has changed, but you feel grey, stale, flat….like you're moving backwards, or just generally confused about your direction. In my experience, this hasn’t been a single stretch of weeks or months, but has cropped up 3 or so times for days to weeks, in the course of the past 2 years. For me, it’s easiest to slide into the Trough when there’s an abrupt change of pace with my workflow. I’ve always found that it’s easy to prioritize when you’re super busy, because you have to be ruthless about what to address first. When all the sudden you have more time on your hands, it’s harder to determine the next critical step, and it’s easy to lose focus. 

 

These are the most dangerous times, because your emotional brain is devious, and will make you doubt everything about your idea, your capabilities, and your choice to take risk in the first place. Basically in these moments your emotional brain is like your closest loved ones- they’re looking out for your needs for food, safety, and shelter, and as such, they’d rather see you throw in the towel and get a desk job with a pension, than stick it out, struggle, and create something amazing that the world has never seen.

The solutions and supports I’ve put into place and used each time this happens have been incredibly simple, and have pulled me out every time. I’m bulleting them below for easy reading.

 

  • Exercise/Have a life Outside of the Business: I’m sure some onlookers have some choice things to say about how public I am with my recreation (most of my personal instagram feed is about rockclimbing, dancing, learning musical instruments, etc), but this is very intentional- it’s not a distraction. Burnout happens when you feel unbalanced, or when you’re making unsustainable sacrifices to reach short or medium term goals. I try to exercise every day- even if it’s for 15 minutes- so I can go to sleep and wake up the next day feeling like a whole person. The endorphins are nothing to sneeze at, and varying things up where some exercise is solitary (eg running on a treadmill) and some is social (like rockclimbing) has been key for me to fill in the gaps where I need it. Having a hobby or interest that is entirely distinct from your business is key too. At times your brain becomes fatigued from focusing on the same issues over and over, and it’s been most fruitful (for me anyway) to take a break and exercise a different part of my brain, before returning inspired and refreshed.
     
  • Keep a Journal: Journaling is amazing, and allows you to translate an abstract emotion (I feel shitty) into actionable data (I feel shitty because of X). If you feel shitty because of a specific situation with the business, you can then outline how to address that specific problem, and take action. If you start writing and realize you just feel shitty because you feel shitty, then you have it on paper in front of you, and your logical brain has an opportunity to speak up and fight back. In my case, occasionally I’ll wake up feeling demoralized about the business, and realize it’s because I slept or was eating poorly, or I had forgotten to pay a parking ticket for weeks and it was lurking in the back of my brain bothering me. It may sound trivial, but the more quickly you can get to the root of the malaise, the easier it is to resolve it and move forward. **One additional benefit of journaling is that it creates an indisputable trail of where you’ve been, and it shows you that you (yes you!) can climb your way out of it. No matter how bad things have been before, you overcame, and here you are today, ready to face your next challenge.
     
  • Listen to, Watch, or Read Stories about Successful Entrepreneurs: I ingest a lot of media on founding, running, and growing startups. I drive a lot, so I’m always listening to a podcasts. How I Built This, and Masters of Scale are my two favorites to play on repeat. They’re very different formats, but I use them to stay inspired every single day. They highlight either full biographical stories, (HIBT) or insights and learnings from incredibly successful entrepreneurs (MOS). In all of these cases, had you spoken to the entrepreneurs when they were first eking things out, they probably would have been stressed, frazzled, and uncertain- but looking back on their struggles and eventual success, it’s easier to visualize your own inevitable success. 
     
  • Surround Yourself with Other Entrepreneurs: This is an invaluable learning I realized very late in the game. For probably the first year we ran Swig + Swallow, I had clustered socializing with other entrepreneurs in the same bucket as formal “networking,” (which I find to be a distraction from “doing my job", and most often a complete waste of time.) What I hadn’t quite realized was that while entrepreneurs may have the least to give in terms of time or resources, in general, they're the most generous and supportive group of people, especially towards other entrepreneurs. Unlike your average consumer, they started their businesses because they saw a problem or opportunity, and have a bias towards action. They want their businesses to work, and they want your business to work, full stop, so they’ll give you that tough feedback, but with the intention of helping you overcome your problems.

    About a month and a half ago I pitched Swig + Swallow to investors on The Pitch podcast (they have about 100,000 listeners internationally,) and the outpouring of support from other entrepreneurs across industries from around the globe has been overwhelming. On the day to day, I can’t tell you how generous all of my kindred entrepreneurs have been in the NY food community. Being able to hear their stories, be inspired by them, and commiserate over shared experiences makes you realize we can ask for help when we’re weak, give help when we’re strong, and together we can take over the world. 

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Lessons Learned in Entrepreneurship: Part 1, "Which Came First, Seeing or Believing?"

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Lessons Learned in Entrepreneurship: Part 1, "Which Came First, Seeing or Believing?"

Years ago I "weaseled" my way into the Wheelchair Design in Developing Countries class at MIT- I was an industrial design student at the Massachusetts College of Art and Design, and was seeking purpose for the skills I was building. I found the Wheelchair Design class on Google, emailed the professor over the summer, and by fall with a lot of research and persistence, had found a backdoor loophole into the class.

We did group projects, and I ended up in the “non-engineer group,” a cluster of super smart students who found their way into the class via other departments (Aeronautics, Management, Math, and so on.) We were charged with making an product to help entrepreneurs in wheelchairs, and ended up deciding on a lockable desk/bag combo. (This ended up being phase one of a project I later adapted into an educational accessory for kids in wheelchairs, but was arguably poorly suited for entrepreneurs in wheelchairs.)

I ended up making the initial prototype of the bag based on the group vision- a flimsy, hand sewn bag that allowed us to piece together the “rough draft” without investing too much time in manufacturing. I remember presenting it to one of the class advisors- a well known professor at MIT. I remember seeing the aghast look on his face- horrified that this was the product of our work in the class. Fast forward a month or two to the final presentation- we presented the final bag and desk assembly, perfectly sewn in durable Nylon, and assembled with custom bent steel frame. That same professor’s mouth was agape- his entire face lit up and he asked, shocked and laughing, “who made this?!!” I said we bent the steel and I sewed the bag, and I realized in that moment that when we showed him the first prototype, he couldn’t see the vision, he only saw floppy fabric and a group of “non-engineers.” He had to see the final product to believe in our potential.

Starting and running Swig + Swallow has been a lot like this. Most people are like the advisor I mentioned- they see a product or a business and view it as static and unchangeable, and have a gut reaction to the product in isolation, in that moment in time. Conversations start getting interesting when we meet people who can envision the future- yes, they take form and function into consideration, but they can imagine the product adapting, the zeistgeist shifting, and human behavior changing,

What we’ve learned in these last few months in particular, is that most of the human population can’t see what isn’t in front of them. This isn’t innately a “bad thing,” but in your entrepreneurial journey, likely 90% of people you encounter have to “see it to believe it.” This can be daunting to the new entrepreneur, but you just have to keep pushing, and trust your gut. At one point not so long ago, “tweeting,” and “liking,” and “ubering,” and “googling,” had no meaning whatsoever….now they are part of our everyday lexicon. Like Danny Meyer said in his book “Setting the Table,” the job of the manager is to keep moving the salt shaker to the center of the table. The employees and the guests’ jobs are to move it away from center, and your job is to always keep moving it back.”

As an entrepreneur, you can’t get disheartened when you put forth an idea and people doubt you or poo-poo the idea.  Will you have to adapt your idea along the way? Yes, most probably. Should you listen to the doubters? Yes, absolutely hear what they have to say and dig deep. Should you abandon your idea if some people just don't get it? Absolutely not. When you're trying to build something original, believing precedes seeing the idea fully realized. It is your job to get a small critical mass to believe, people will start to see, and then you get to connect the dots... to realize your vision in a way that meets the the needs of your audience.

Just like in the example above, when faced with someone who can't see the vision, it is your job to keep pushing, keep iterating, and keep adapting until you see their eyes light up with understanding.

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Tell me what we're doing wrong, please

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In the year and a half Swig + Swallow has been in business* we’ve received 3 complaints about our product or shipping issues, and 2 calls where people were confused about the shipping option they chose.

That’s it.

Over thousands and thousands of bottles sold, and many thousands of samples tasted, you’d think that would be a good sign.

But it’s not.

You see, our company, Swig + Swallow produces fresh cocktail mixers for iconic cocktails, like the Margarita, Moscow Mule, and Mojito. We are the first mixer company to intentionally half-fill the bottles, leaving room to add spirits directly to the bottle to complete the drink, no measurement required. As veterans of the cocktail and spirits world, my co-founder Gates Otsuji and I know this is the best way to drink craft-quality cocktails at home. Not only are we providing the same fresh ingredients you’d find in the top cocktail bars, but we’re perfecting the balance between citrus, sweet, and natural flavors, so you can just add your spirit of choice to the line on the bottle, and poof, you’re done!

But back to the problem.

Especially because we’re first to market with this concept, we are thirsty for feedback (no pun intended.) We know when we sample people on our product, they love it and they buy it. Press has been good to us too, so we’ve been lucky. But most friends and allies are unreliable, because they will tell you the great things about your product, and leave out any bit of criticism, regardless how small. And, what people don’t understand is that feedback is the most valuable asset we could have…without it we have vision, but we move forward with blinders. 

Besides the thousands of conversations we have with consumers and trade alike, we’re looking for other ways to encourage this feedback, and we’re open to any and all suggestions on how to cultivate more of this. We installed Yotpo into our site this week to host public reviews, and we earnestly want honest feedback. If you want to help us bring you the best product possible, please either review us on our site, or if you’d prefer, send us private feedback using the contact page on our site, or by emailing me, april@swigandswallow.com

Seriously, tell me what we’re doing wrong, please…. 

 

Many thanks!

-April Wachtel

Founder/CEO, Swig + Swallow

 

*With this business model- technically I ran this as a B2B service for spirits companies and catering companies prior to 2016.

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