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What Would You Do Differently?

I met an entrepreneur recently who is approaching a similar market and product that I once did. Before meeting, he realized I had written a book, so read it beforehand. It resonated greatly for him. As we met, he had a few specific questions including: “if you could do it all over again, what would you change?”
There was a lot I would change as I’ve outlined on this blog and in Postmortem of a Failed Startup: Lessons for Success. There are always ways to improve. But one major lesson stuck out at me – start out smaller, more deliberate. Start out with a very specific product addressing a very specific pain.
This would invariably lead to quicker rollout of the product. This would lead to quicker feedback. This would lead to quicker iterations. This would lead to… success? I’m not sure, but I feel this approach would have been much smarter.
Success does not follow a formula. The most brilliant minds have failed. It’s critical to fail at times, too. But the approach to success can be tuned in to mitigate risk. I think my big take-aways after all these years also line up with being loved by customers (the product, at first) to create something wanted… needed. With that, I want to tackle opportunities with a focused effort and building something that enables my customers that also aligns with my vision in mind.
Looking back at your ventures, what would you do different?
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Risk-Reward vs. Success-Failure and Others Lessons from a Serial Entrepreneur

Serial entrepreneur Gregg Oldring recently wrote a post about his recent startup that failed – “Afraid of failing at a startup? Let me tell you what it feels like.” Naturally, I wanted to dive into the title given my past.
There were a couple lines I really enjoyed. Sharing those here, and highlighting my own experience.
  • “When I frame the analysis as risk-reward instead of success-failure, we did well.”Maybe because I failed before with Body Boss, but this was incredibly resonating. Like Gregg highlighted, there was so much gained from the experience that isolating the outcome based on commercial success would be vain. In the end, we threw out risk to attempt something special. The reward beyond was worth it.
  • “One of the things that I hate about being an entrepreneur is that sharing the uncertainties I have about my business usually carries with it negative consequences that outweigh the benefit of transparency. When someone asks, ‘How’s business?’ the answer can seldom be, ‘It doesn’t look like it’s going to be sustainable.’” Geez, this ateat me towards the end of Body Boss. I felt like a fraud when I spoke to others – prospects, yes, but especially with my personal connections (friends and family). The weight of faking a smile was heavy. So heavy, in fact, that I avoided any discussion about the venture as much as possible.
  • “I’m not embarrassed or ashamed that Inkdit didn’t thrive. My friends, family and community haven’t made me feel that way. In fact, they’ve done quite the opposite. I’ve been reminded that I have many people who support me.” As the dust settled from shutting down Body Boss, friends and family came from everywhere pledging support. It was humbling. In many ways, too, I was proud. Many applauded our courage and how we built something from nothing.

Gregg’s experience from failure sounds a lot like mine. As I read the comments to his article, I’m reminded of the power of sharing unsuccessful stories and being vulnerable. Confidence in what we’ve achieved and where we’re heading gives us power to go again. Sharing our stories gives others the confidence and support they, too, can go for greatness.

By the way, you can read more about my experience from my book Postmortem of a Failed Startup: Lessons for Success. It’s a quick read so you can learn, apply, and go (e-book and paperback available).
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The “New Normal”

Atlanta is notorious for stress-inducing traffic, and it’s going to be even worse since one of the busiest roads collapsed on March 30th due to a fire.
Collapses (read: “failures”) have their way of teaching us. So, I want to take a moment to share a few reactions from this debacle.

Enabling New Day-to-Day Experiences

Atlanta’s traffic is well known, but to be honest, traffic is on par with other major cities. The difference is perhaps volume due to our limited public transportation options. (And poor take-rate for the options that do exist.)
This new challenge will motivate many daily commuters to try travel alternatives. The key here is how this will affect the day-to-day. By integrating public transportation into the daily lives of so many for an extended period, commuters can more accurately reflect on how public transportation can affect their lives.
Too often, in the past, public transportation services like MARTA have discounted transportation for special events. Commuters for special events, then, rarely consider MARTA for anything but special events. They certainly would not associate the ease of daily commuting when their limited experience includes jam-packed trains.
Forcing the day-to-day can be a real eye-opener for many.

This is the New Normal

Mark McDonough, commissioner of the Georgia State Patrol’s Department of Public Safety came out asking commuters to be patient citing repairs could take months.
One of the best parts about his address was cutting to the chase – “… get up earlier. Find a new route. This is new normal.” There is no value in whining and crying about what happened. It’s happened. Adapt.

Where and What We Can Learn from Collapse

There was a joke going around that this was actually the second major Atlanta collapse this year – the Atlanta Falcons’ major Super Bowl crash being the first.
Atlanta entrepreneur Jon Birdsong shared this post – “Why Atlanta’s Collapse(s) Are Good For Us”. In this post, he reflected on how the Falcons’ collapse made him reframe resiliency by studying the orchestrator of the greatest Super Bowl comeback ever – Tom Brady.
Birdsong read books and articles about Tom Brady, and adapted much of his own lifestyle to be more like Tom’s. Everything from daily habits like diet and exercise have changed Jon for the greater. Birdsong credits the Falcons’ loss as the motivator.
Had the Falcons won, Birdsong would have been ecstatic and hugely supportive. However, the loss has given him a new way to look at life beyond the game.

Life happens. Sh!t happens. Adapt, and keep going. This is the new normal.
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Postmortem of a Failed Startup – Now in Paperback!

Today’s post… a plug for my book – Postmortem of a Failed Startup: Lessons for Success – is now in hardcopy! You can pick up the paperback on Amazon for $13.99 (or ebook for $5.99).
I originally published the book as an ebook in early January. Got a lot of great feedback including Amazon reviews like…

I want to start using the book to teach other entrepreneurs before meeting with me. One of the reasons why I wrote the book was because of how often entrepreneurs shared challenges described in the book.
If you’re looking to get your venture off the ground, your idea out of your head, or have a startup in-flight looking to grow, get the book on Amazon.

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Entrepreneurs and Artists – What Keeps Both Going

I recently met an author of several books and also had a startup some years before. She lamented how her beauty product was probably too early – timing, indeed, is an important factor in startups. She also shared how many of her books failed to be commercial successes.
Knowing what my own book was about, she asked me, “When did you know it was time to stop?”
I get asked this a lot. Perhaps everyone believes an author on startup failure knows the moment. Perhaps I know the signals, the omens of impending startup doom. That, sadly, is not true at all. It’s not true because there’s no answer. It’s up to the entrepreneur(s).
Steve Blank used a comparison in “Venture Capital is ‘Liquidity Ponzi Scheme” that I often use: “entrepreneurs are like artists”. Both can accomplish great things and be wildly successful. Both can be wildly misunderstood, too. Both, likely, must overcome the roller coaster of ups and [many more] downs before finding success (if ever).
Entrepreneurs and artists are driven by a mission and passion. That’s what keeps entrepreneurs and artists going.
Entrepreneurs, like artists, see the world in their own ways (“different”). Often, they misunderstand or meet odds and antagonists all over. To entrepreneurs and artists, the challenges are opportunities.
When I looked at the author, I responded, “you stop when you’ve lost the passion” referencing what happened at Body Boss. We had lost the passion to keep hitting and overcoming challenges.
A Google search of “failure” and entrepreneurs returns thousands of results, and indeed, entrepreneurs. Jack Ma, founder of China’s Alibaba, is one such example of extreme grit and persistence – his failures are well-documented. When entrepreneurs ask, “when do we know when to quit?”, they are looking for reasons to quit. Many are looking for outside influences to signal to stop when the true answer lies within.
You’re going to run into challenges (opportunities) as an entrepreneur or an artist, no doubt. What will keep you going is passion and a belief in your mission.
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6 Take-Aways From My F-Up Talk

Last Thursday, January 14th, I had the pleasure of speaking at the second Atlanta FuckUp Nights event. FuckUp Nightsis an organization in over 150 cities with events highlighting stories of failure. The format includes four speakers each with 10 slides that auto-progress 40 seconds each.
The organizers expected 65 in the crowd, but we kicked off with over 100. Needless to say, the organizers, Tim Adkins and Jay Cranman, did a great job getting the word out.
The talk went fantastic. I got a lot of great responses including many who related to my story and learned a lot. Take-aways from the experience…
  1. I had seven consecutive black slides that looked like one slide with the auto-transition. This allowed my story to flow without sticking to a rigid format. (Hey, I’m an entrepreneur – I disrupt things.)
  2. Rehearse, rehearse, rehearse. My friends in the acting world pushed me to rehearse… a lot. Happy they did as I didn’t struggle at all in the talk. Everything flowed real well and natural.
  3. Write a script, rehearse the script, but don’t follow the script. I wrote down word-for-word what I wanted to say. However, I didn’t once recite the script verbatim. I just let my mind speak with whatever it wanted to as long as the message was clear and the point was clear.
  4. Prepare for post-talk questions. There was 5 minutes following the talk for Q&A. I forgot to prepare for potential questions, and though, I knew my answers, I could’ve answered more succinctly.
  5. People really pulled in when I shared a vulnerable moment. Given I was talking about a very passionate, sore subject, I did get choked up at one point. My book’s collaborator, Don Pottinger, suggested this, and I’m glad I listened to him. The result was my story resonating really well with the audience.
  6. ALWAYS consider the audience. As speakers, our talks were our products. Our market was the audience made up of those in technology, startups, and those completely foreign to technology. This meant our messages needed to be adjusted to be easily understood by everyone (read: don’t get too technical).

It was such a fun experience speaking, and I hope to do many more in the future. Stay tuned!

What are some of your tips on public speaking? How have you prepared?
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My Life-Defining Moment Happened When I Failed to Make Varsity in High School

Just because a few doors are closed, doesn’t mean one won’t open later. (image source: http://cdn.h3sean.com/wp-content/uploads/2010/05/Closed-doors1-300×197.jpg)
Ever stop to think about who you are? What makes you tick and tock? How about what you truly enjoy and what you’re good at vs. not good at? Or what/ who has shaped you into the person you are today?
I’m at this stage of figuring out whether to continue independent consulting while iterating on ideas for the next startup or take on some full-time employment (consulting, product management, or otherwise). My recent post about my daily/ weekly schedule was an interesting exercise in stepping back and recognizing what I’m actually doing in a day, and made me really think at the macro level.
In one of my recent reflections, I thought about defining moments in my life. One of those watershed events that truly transformed me was my failure to make the Varsity soccer team in high school. I won’t rehash the whole story here – shared the story almost a year ago in my post titled “Getting Through Dark Moments and the Most Vulnerable Story I’ve Ever Told Publicly”. It’s this moment that I would say was a major Defining Moment in my life.
Dictionary.com’s definition of “Defining Moment“
I remember that day in high school so vividly… it sucked, for a lack of a better word. I was crushed. Soccer was my life. Sure, I apparently wasn’t so great at it, but I loved it. I played every day. I had aspirations to be a pro one day. It’s true what they say, “you learn more from failure than success”.
As I think back to that moment and my life since, I can distinctly see how it’s shaped me.

Consistency – it’s what separates the good from the great.

Actually, the Varsity coach told me this was a major reason for my exclusion. I played well, but I wasn’t consistently playing well with errant passes or poor positioning. When you watch the great players, they were consistent in their play. They were dependable center backs who you could rely on to make that last-ditch stop, if needed. I just wasn’t dependable.
In entrepreneurship for me, this plays out in my interactions with others, being on my toes ready to pitch at any moment, maintaining a cadence with customers, etc. I strive to maintain consistency in putting together high quality products and presenting myself to the highest level.

Details – it’s also what separates the good from the great.

One of the other aspects of the great players who made the Varsity team from the others was the subtle details in their play. I remember one of the center-mids on the team had such amazing field perception that he knew where everyone was on the field. He had some Spidey Senseof when an opposing player was coming up on his back. The best players weren’t just passing, but were passing with enough oomph and in a direction that would allow the receiver to move WITH the ball and away from an oncoming defender. This is kind of like the best quarterbacks in the NFL who lead their receivers with a throw, away from the onrushing corner.
From a professional standpoint, paying attention to details means checking for spelling mistakes. It’s ensuring logistics are nailed down for any meeting or get-together. At Body Boss, for example, details included doing reconnaissance work of a school and the strength program I was visiting. It meant ensuring all the marketing collateral was ready before a coach’s clinic.

Be Aggressive. B-E Aggressive.

(Thinking back to my high school days reminded me of this constant chant at football games. That’s funny, right? No? Okay…)
I remember my earlier years on the JV team when I played incredibly conservatively. I was naïve and hadn’t played at a high level like some of the others. I distinctly remember one player who had played in the highest echelons of youth soccer (beyond Classic 1 – some summit I didn’t know anything about). I had the ball running in one direction, and the player was defending me. Except, he just brushed me aside, and ran off with the ball. I just witnessed the football “swim move” but on a soccer pitch. I thought it was a foul, but it was perfectly legal. I was just weak.
Today, that mindset of being aggressive and strong pervades me. If I’m not, others who “want it more” will grab opportunities leaving me in dust. If you want the ball, if you want the sale, you need to “swim move” your @$$ in there. Don’t play conservative…

If you’re not confident, you’re not going anywhere.

Kinda like the above point, but aside from being aggressive, having a mindset of confidence goes a long, LOONNNGGG way. Be confident in your abilities. Be confident in who you are. Be confident in others.
I remember I always looked up to those guys who played in much, much higher levels than me. They carried themselves like they owned the pitch, and compared to me… they did. I looked up to them like I was a small fish, and when I thought like that, everyone else did, too.
It’s hard to get others to believe in you if you don’t.

Bad outcomes don’t mean bad outcomes forever… and short-term memory is great.

I wanted to parse these two into different bullets, but they go together so darn well. Plus, it’s the most important point here.
At the end of the day (or in my case, my high school years), I didn’t make Varsity my Junior or Senior years. Boom. Didn’t make it. Enter college, though, I eventually made it to the Georgia Tech Club Team’s A team. I even captained a team one year. Since then, I’ve played on teams that have won leagues and divisions from Atlanta Division Amateur Soccer League (ADASL) to Silverbacks and various tournaments. I’ve played with some amazing players from all over the country, and my best friends are from these years.
I loved soccer so much that even as I failed to make Varsity, I kept at it, and eventually, I was in with the soccer crowds I wanted to be a part of when I was younger. I failed to make the teams prior, but then some really great things came about later because I learned from those earlier playing days, and I kept at it.

The take-aways…

It’s funny taking a step or two back to look at the grander picture. For me, I looked back at a terrible moment of my life, and found a lot of positives that came from it. I lost a couple battles in high school, but so far, I feel I’ve been winning the war.
Thinking about it perhaps more philosophically, the ­failure of not making Varsity doesn’t define me. It was the lessons from failure that defines me, or maybe just helps define me.  

Take 10 minutes out of your day for yourself and think about this – what was a defining moment in your life? Why? How has it impacted you today? 
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Without Product-Market Fit, Did We Quit Too Early?

Reflecting posthumously… Source: http://news.bbcimg.co.uk/media/images/64480000/jpg/_64480391_sunset_rocks.jpg
If the inner voice in you keeps telling you to go back or to keep forging ahead, should you? Should I?
I keep bringing up Body Boss recently because I feel it’s unfinished business. I feel like we quit too early. Or maybe I’m just really passionate about it still. Or maybe I still get messages from happy customer-partners who want to continue to do more. Or maybe I’m crazy and I’m blinded by the potential opportunities to see the actual lack of opportunity.
There’s a popular picture I’ve seen illustrating the cost of giving up too early:
Source: http://www.davidmcelroy.org/wp-content/uploads/2012/01/Three-feet-from-gold.jpg
For the myriad of lessons learned in 21 Rough Lessons Learned from Failure post, I still can’t shake that maybe we stopped building Body Boss too early for ONE major reason. In fact, Marc Andreessen shared the idea recently in “On product/market fit for startups“:

“My contention, in fact, is that they [startups] fail because they never get to product/market fit.” – Marc Andreessen

In the article, Marc was referring a lot to the market being the determining factor of startup success as the market can actually pull a product and team in the right direction. At least, that’s my simplified synopsis. However, this notion of failure before product-market fit is an incredibly resonating one.
In the 16 months following launch, we had over 70 unique schools/ programs trial Body Boss, and we had 12 paying customers with about 4 of those signing back up. Yes, these are paltry numbers. However, if you look at the data from interviews as to why they weren’t subscribing or why they didn’t re-subscribe there were very, very common reasons. The market was trying to pull us in the right direction. We just resisted.
In fact, 3 of the 4 re-subscribers were actually in months 10-14 when we started to build some of those features customers were asking for. (They re-subscribed after we announced the zombification of Body Boss, actually.) However, in the end, we made a collective decision to not pursue Body Boss as it stood.
“So what are you trying to say, Daryl?!” I’m saying this…
  • Capture data, and you can start to see a story. For us, it was poor product-market fit at the beginning which could be explained, largely, by a lot of hubris on our part (we thought we could be like Steve Jobs and tell coaches what they really wanted) and by poor customer discovery up front.
  • Speed kills… or rather, lack of speed. If I could, I would’ve funded the team so everyone could be full-time on Body Boss, and thus, no other distractions of full-time employment elsewhere. Without distractions, perhaps we could have churned out the right features and user experience [quicker] to reach closer and closer to product-market fit.
  • Have Empathy and Let the Currents Take You. As I mentioned above, there were many moments we, as a team, failed to listen to our customers. We naively believed we knew the better way to do things. We lacked empathy, and even though the market was trying to pull us in the right direction, we didn’t let it. When enough of the market tells you to move one way, you have to put aside your ideals for the greater good.
  • Failure/ quitting is always an option. I don’t want to say “quitting” is always a bad thing, because sometimes, it’s the right thing. Like I said before, I could be blinded by what I believe is there. That’s why having a great team is important, too… to not just say, “YES” to everything I say, but to challenge me.  
  • Regret is a damned thing that can haunt you, but you have to move on. The experience with Body Boss has taught me a great deal on startups, about building a team, and much more documented in the 21 Lessons Learned. However, in corporate settings, a failure is a failure. In startups, failure is called experience. Embracing the lessons learned will give me great hope for the future.

Of the 70 schools who signed up for trials, but didn’t convert, I’d say at least half of those would’ve subscribed had we nailed a few items down ranging from a rework on user interface to features. That’d give us about 40-45 customers in the first 18 months – not too bad. That’s my expected benefit. Conservatively, 20 schools would have converted – still not bad, and I’d venture to guess many more would re-subscribe, too.
However, features aren’t always going to win over customers, I know. That’s why I’m suggesting this based on my actual conversations. Perhaps designing for the users would also have helped move a low-tech industry to embrace more technology… or maybe we would’ve died anyways. There are a number of things we could’ve implemented, too, to help really mitigate against building the wrong product such as Letters of Intent, development alongside customers, a system by which customers/ prospects can request or reserve features almost like a Kickstarter (it’s in my head how this would work), etc.
I suppose that given we never reached product-market fit and looking at the data posthumously… I can’t help but wonder the WHAT IF. I ask myself whenever I finish a project or day if I killed it (in a good way). I don’t feel like we killed it for Body Boss. I think we could’ve done better… that’s a pretty bad feeling, but one that I have to learn from and move on. Right now, our competitors are making large headway in the market, and the opportunity has largely passed by to revive Body Boss and be the dominant player. Lack of speed kills.
For now, Body Boss will be one of those opportunities with great regrets and great learning moments to take to my next startup.
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Life After Failure: Stories from the Founders

(Image source: jewschool.com)
My buddy (and the great Developer) Don sent me this link from HackerNews where a user posted the following question:

Founders whose startups have failed, where did life take you afterwards? (link)
I’ll just cut to the chase today because I read a ton of the responses… almost too many. I got through about 80% of comments, and I think I’ve got enough content in my notes to cull some of the interesting stories and take-aways.

“Hacker News is a social news website that caters to programmers and entrepreneurs, delivering content related to computer science and entrepreneurship. It is run by Paul Graham’s investment fund and startup incubator, Y Combinator.” – Wikipedia
So here’s the list. Though, note that this is from the first 33 posts as of 9:30AM this morning (11/12) (not including replies to comments here, just first-level comments).
  • 8 founders I would qualify went into full-time gigs with seemingly non-startup companies including many at Apple and Google
  • Many cited regaining confidence and stability as a for joining a full-time role at a non-startup company. One described the failure experience as “traumatic” to the extent he questioned his skills and capabilities. He needed a place to rebuild his confidence.
  • 8 founders went immediately into some consulting or contract work. Many cited reasons including having flexible hours to the extent that they worked half-time. The other “half-time” was spent on side projects
  • A couple of the founders made note of the incredible stress the startup life took on their personal lives to the extent that their relationships ended either in divorce or otherwise. Interestingly, one of them got back together with his then girlfriend and married after the startup’s initial failure
  • Several founders mentioned the people involved as a reason for the failure of their startups from co-founders to employees. On the flipside, there were a number of founders who mentioned they would or have start a new company with their former co-founder
  • Cultural insight – one founder in Germany mentioned how difficult it was to regain some stability after his startup’s failure. In German culture, much weight is put on success and respect, and from failing in a startup, it was hard for customers, colleagues, etc. to accept this reality or trust him
  • Cultural insight – one founder in India mentioned how he was buried in debt to the extent that all profits were made to pay down interest to his lenders. In India when borrowing for business, many borrow from friends and family (close and distant). This can dramatically raise the interest with the number of borrows
  • HackerNews has a very much technical-heavy audience, but at least two of the founders mentioned their complete lack of technical know-how in their startup. Following the demise of their startups, these founders learned how to program to build MVPs including one founding a new startup as a technical co-founder
  • In trying to decipher what people were explicitly and implicitly saying, at least 23 of the founders said they would start or had already started another company; 4 founders I couldn’t figure out if they would (categorized these as maybes); and the remaining 5 founders as most probably not interested in starting another.

There’s a lot more to glean from the comments and posts, especially when you look beyond the first-level comments. It’s interesting to read about others’ failures to hopefully avoid those missteps. However, as several readers mentioned, it’s hard to avoid even when you know them. Experience should help prevent you from making those same mistakes, but there are blogs and established publication articles about lessons from failure including my own – 21 Rough Lessons Learned from Failure. As user nostrademons mentions, “The nice thing about having knowledge and experience is that oftentimes it shortens the time required to realize you’re making a mistake.”
Okay, so I’ll leave you with a few direct quotes that I thought were important…

“Someone may be a good developer, designer, or co-worker…but that doesn’t mean they will make a good co-founder. I learned this the hard way..and it was painful” – paulhauggis

“All I can say is: Know your founders. I’d go far as to focus on their personal situation, like their risk tolerance, their “philosophy”, their personal attachments, etc. The goal for a company is not to save the world, but to make money for you and your partners. If any personal attachment can get in the way, like “saving the world”, or “keeping control of the company”, it will. My major failure was not seeing this.” – bigpeopleareold

“A startup is a ship at sea in a storm, I wanted to experience a boat in harbour for a while.” – buro9

“The nice thing about having knowledge and experience is that oftentimes it shortens the time required to realize you’re making a mistake.” – nostrademons

“Focus on one thing , become incredibly good at it. […] Focus on customers and trust yourself on giving value , customer insight is better than customer need.” – appreneur

So what are your thoughts on the lives after failures for these entrepreneurs and others? How do you think failure has changed their trajectories had they either not pursued their own startup(s) or had been successful?
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A Case Against Entrepreneurship and Pursuant of Passions

Another Daryl Lu original (powered by Microsoft PowerPoint)

Okay, if I were to really pursue the dream that made me happiest, I’d be fighting my way into Jurgen Klinsman’s squad for the World Cup coming up on Thursday. (!!!!!!!!!! Super stoked about this!) But I’m not because there’s a gap in skill (maybe) and of course, the cost-benefit ratio/ opportunity costs to think about. There’s a graphic out there on the interwebs describing the crux of what most everyone falls into…

(Source: https://bobbiblogger.files.wordpress.com/2012/04/rich.jpg)
This is a good portrayal, I think, in the world of Venn-Diagrams telling you what to do. However, I think we should step back a second and assess where really you want to be. In most cases, I think it’s being happy and if you were [knock-on-wood] to pass tomorrow, would you be satisfied? Or, what regrets would you have… how do we minimize regrets?
The buzzwords today are “entrepreneurship” and “startups”, and with the Hollywood flick of The Social Network about Mark Zuckerberg and Facebook, along with the many success stories we hear about including Snapchat’s $4B acquisition offer by Google, WhatsApps liquidity event at $19B to Zuck and Co., and others, there’s obvious stardust in our eyes to dream big. That, and we all like to think we can be billionaire bosses. The truth is, though, we can’t and most aren’t.
Having spent the better part of the last few years making no money on a startup (even as a tech firm with low costs, there’s still some costs to cover) and then shuttering, we’re still one of sooo many stories of unfortunate failure and like I said, no money. You know how media goes, though… in the world of startups, hype up the big acquisitions and startup successes. That sells.
But looking at this gorgeous wedding this past weekend I attended in Jamaica, it also brings about a harsh reality some (many) entrepreneurs face… without income, you limit yourself on what you can do or how much you can enjoy things. It’s a hard road going uphill while most of those around you are in cushy positions living it up in otherwise more stable occupations. For me, I’ve traded the lavish lifestyle of consulting (let’s tone down “House of Lies”, by the way) for the uncertainty of startups.
It’s definitely sucked to go to bachelor parties at nice steak restaurants (my favorite), and hold back or not order anything at all while the rest of the group chows down on glorious meaty plates.
Luckily, I’ve got some runway from savings from years of lavish consulting and still frugal spending. However, for the last several months, I’ve eaten countless loaves of bread with peanut butter for lunch and I’ve stopped taking my whole family out to dinners just because… instead, it’s my family definitely supporting my dreams (me).
In fact, an entrepreneur once used the term “mortality of an entrepreneur” as a reason why he seeks funding for any of his endeavors. He only has so much to keep going on personally. Not that I can say I want to be beholden to someone else, or really have a living off another without a really good, profit-generating business, but it’s interesting to think about.
It’s a tough life, and one day, I hope to pay back my family and friends for the support with dinners, random gifts, vacations with friends and family, etc. For now, I’ve got to watch the wallet (especially from homeinvaders at night), and keep plugging away with the belief that I’ll pivot and find my entrepreneurial success to give me the stability and flexibility we all really crave. I don’t think financial security necessarily gives us the “freedom” we want as much as we want the “flexibility” to change our directions.
I know several friends who say they want to do their own thing one day, which could very well be true. However, looking at their lifestyles right now, you can also see how a job is just that – a job. It doesn’t come back to bite them at night. It doesn’t keep them up. However, their jobs enable them to have and live a lifestyle they’re completely happy with.
Entrepreneurship certainly doesn’t guarantee happiness, much like a current “corporate” job. If in the end, you’re happy and your job enables a lifestyle you’re happy with, you’re able to travel the world like you’ve always wanted, then that’s okay, too. We should all be okay with that, rather than push into the media-hyped world of entrepreneurship and startups.
So if you think you want to be an entrepreneur, it’s important to really understand the difficulties and be strapped in for the long run. At least for me, I subscribe to the idea of “plan for the worst, hope for the best”. At some point, if the money doesn’t come through one of these entrepreneurial endeavors, there’s going to be a harsh reality for me to mitigate my risks while perhaps embarking on a journey that may take a step back toward entrepreneurial greatness. It sucks, but taking two steps forward and one step back is still better than no steps forward.
And before I close this article up, I do have to include the obligatory bulleted list of some pros of the harsh realities of entrepreneurship:
  • Lack of income creates some creative solutions
  • Having a set meal everyday frees up time thinking and shopping for what you’re going to eat
  • Like a dog backed into a corner, you have to fight to survive
  • Without stable income, you find you can cut out a lot of extraneous niceties (#firstworldproblems be damned!)
  • Most people will never understand what you’re going through, but with a strong startup community, you’ll find a niche of those who have gone through it, ARE going through it, or will
  • You emerge from the darkness with incredible strength and mental/ emotional fortitude (I hope)
  • If you’re like me, you thrive on challenges and building something from nothing. Entrepreneurship is certainly ONE avenue to do so, and the one I’m using as a vehicle to make a bigger impact. You can find yours, too

Without great risk, it’s difficult to attain great benefit, and so yes, I definitely still view full-time pursuit of a dream is the way to go, but like I said before, it’s wise to mitigate risk through preparation personally (familial), financially, professionally, mentally, emotionally, and socially (all the other -ially’s). So if entrepreneurship is going to make you happier or help you get there, by all means, do it. If it’s not, then do what you can to achieve what makes you happy.

What are your thoughts of why you shouldn’t pursue entrepreneurship or some other passion? What are the cases to overcome the risks involved?
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