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At The End of My 2.5-Year Startup Roller Coaster: 21 Rough Lessons Learned from Failure

Yowza, starting a startup from nothing is wicked hard. After 2.5 years at Body Boss, my team and I have been riding the startup roller coaster with high highs and low lows. Our ride has been one of the most frustrating, stressful, challenging, and rewarding experiences of our lives. A ride that sadly stops here.

We aimed at curing time-consuming spreadsheet madness and bringing intelligence into a world where technology feared to go before – the gyms of high schools, colleges, and the like. We made pivots to our dream, but sadly, we won’t be continuing further. Our market is incredibly young, and though growing, does not provide a sustainable operation for the foreseeable future. So as it stands, we'll be supporting Body Boss as it is today, but unless/ until the market matures, we won't be building out new features or spending heavy resources on marketing at this time. 

As they say, you learn more from failure than success. And boy have we learned… If you’re looking to start your own venture, the below list of 21 lessons we’ve learned should help plot out your course and watch out for traps. Or in the least, these lessons can save you from punching helpless pillows or picking up all the papers you threw in the air from frustration:
  1. Have customer-PARTNERS at the beginning. Partners at the beginning give you momentum coming out of the gate to not only build the product, but also to sell the product. Social motivation is a powerful tool.
  2. Research should weigh heavily on building your product/ service WITH your customer-PARTNERS. Engaging your customer-partners early and often (in an effective way) will mitigate risks you’re building something that they don’t want, need, or it’s just too far outside the process. The first versions of your product/ service will need refining, and communicative partners will tell you how to improve.
  3. Dedication to the startup is clutch to iterate. I’ve said it in a post before that speed is one of the critical elements of a winning startup strategy. With speed, you can iterate through ideas and test them with your customers. The best way to do this is to work full-time on the startup and have high quality engineers/ developers. Quality builders can implement changes quickly and mitigate against the risks of glaring bugs.
  4. For a tech startup these days, design is the second part of the winning strategy. If it isn’t quick to understand and navigate, users will likely not give you the time of day to figure it out.
  5. Quick set-up is the catalyst for early success. Apps these days that sign up and login with Facebook, or have API implementation with big platforms like Salesforce.com can help customers get set up quick. It turns out to be a turn-key solution. Most people don’t want to take precious time to learn or set up a program, especially when they have an existing, albeit weaker, solution.
  6. Establish an effective method and rhythm to reach prospects. With social media, many people believe it’s the best way to reach new customers. But it’s not necessarily. You should know how your target market absorbs new ideas/ products. Do they read magazines? Do they read blogs? Are they social media users? Your marketing strategy may not make sense.
  7. Don’t believe you’ve made a sale till days after a check clears. Can’t tell you how many prospects said they’d buy only to go cold a day later. And even when someone gives you his/ her credit card information, wait for the amount to clear your bank account before you celebrate that new signing.
  8. Establish roles be it with titles or equity. It’s amazing what happens when everyone is equal and everyone has different ideas – wheels spin but you’re going nowhere. I applaud those avant-garde companies trying out flat orgs with “no titles”, but that’s not for me. In Body Boss, we had 4 Co-Founders -- equal shares, no hierarchy... just friends. To have a single, clear vision to fall back on when consensus isn’t there is a beautiful thing.
  9. Treat your startup like a real company. Your startup is not a hobby. It can't be a "project" if you want it to be something greater. It’s a company. Take it seriously. Everyday you aren’t improving your company, everyday you’re not making your product or service better, you’re wasting your company’s talent and resources. Sadly and ironically, that happens to be your own.
  10. Market like a king with a blacksmith’s earnings. If you’re going to spend any money on marketing like attending trade shows, make sure you standout. We once sponsored a dinner for an event thinking it'd be a great way for us to reach prospects, except it didn't. Everyone just ate and barely heard our message. That's a good bit of money down the drain. If your hard-earned dollar isn’t going to WOW and prompt your prospect to the call to action (CTA), don’t bother.
  11. Be ready to pitch anytime and everytime you walk outside. It’s an amazingly small world, and you will run into potential customers, investors, or just everyday people who can connect you. Be ready to pitch.
  12. All about the team. To have diversity in a team is incredibly frustrating. However, it’s beautiful. It’s needed. For success, you need people to debate productively. If you don’t debate new, fresh ideas from your team (not just customers), you may be potentially paddling down a waterfall in unison. Diversity forces you to sometimes build only what’s necessary, and cut out the fat unless there’s true value. That, or you may never get those new, fresh ideas at all.
  13. New sales are good, but recurring sales are better. One issue that we found at Body Boss was many customers subscribed and bought in, but then, didn’t re-subscribe. After talking to many, there were various reasons why it didn’t work out including glaring product-related issues that we weren’t aware of. If they don’t sign back up, find out why because marketing a product that loses customers later can crush your business. Existing customers can be powerful advocates, and word-of-mouth marketing is the best type of marketing.
  14. Solve a real problem. Definitely don’t introduce a new one. So much of the above can also be addressed if you solve a real problem. With a real problem, you’ll get the buy-in from prospects to buy what you’re selling, or work with you because in the end, IT’S A PROBLEM!
  15. Pick an industry where you have LOADS of experience can go a really long way. Not only to give yourself and your startup credibility, but it’s a great way to network and find your initial customer-partners. I think one of our struggles at Body Boss has been because we approached professional strength and conditioning within an institutional setting – a setting none of us have had much experience. Thus, we didn’t understand our customers as well as we should’ve to build and sell our product.
  16. Know your limitations, and when to break them. Not all of your customers will buy into what you’re selling. Not all of your team members can work full-time. You might not have the skills to pick up the keyboard and start coding. However, all of these challenges end up being opportunities to build a greater startup, a better product, and a better service. If you pay attention to those limitations, you may be able to find creative solutions around (or through) them.
  17. Know when to stay rigid, when to flex, and when to break on your ideals. We start companies with the confidence that we can do things better. By that very nature, we enter with ideals. Know when your ideals should stick or when they should take a back seat for the growth of your company.
  18. Don’t make excuses. Just sell. My main role in Body Boss is to sell. I catch myself sometimes saying, “oh, it’s hard because of timing” or “they’re not answering their phones, so… yeah”. It’s admittedly poor. If you feel an inkling like you didn’t bust your @$$, then you probably didn’t. Find the value. Convert.
  19. Measure everything you can within reason. Use Google Analytics to track your website traffic. Analyze user engagement data (effectively, not analysis paralysis). Track by device, by user, what is your customer doing? With data comes the ability to draw patterns and make actionable changes. “What gets measured gets improved.” (That’s actually a Trademark we have.)
  20. It’s your company so choose who to hear and who to listen to. Everyone has ideas. Everyone will give you advice whether you want it or not. Know which ones make sense. It’s your company. You have to make the calls.
  21. SALES IS HARD! At the end of the day, companies, teams, etc. are made of people. And because you’re selling to people, it only makes sense that not everyone will be seeking the same values out of your product. It’s best to learn quickly about your prospect when selling, and catering your value prop accordingly. A couple tips: (1) the international language and what everyone wants more of: money. Help them pull and push the lever to add revenue and/ or cut costs. (2) You have two ears and one mouth. Let your prospects do the talking so you can assess what he/ she needs, and they’ll be bought in. (3) In-person goes farther than phone or email. Also, emails suck. Too easy for customers to delete/ not read.
Are you ready for the ride? Have you perhaps fallen victim to any of these hard lessons? What advice would you give to entrepreneurs?

(Also, how fitting is it that I’m petrified of roller coasters? They freak me out.)

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