Hard Knocks for Hard Chargers

June 2019 marked a very important milestone in my journey to transition to meaningful work in tech startups (SaaS/Fintech). I made a full shift in my mindset from the involuntary fear that grips me when I feel out of my depth, to the visible confidence of someone who is prepared for the long haul. It took six months, but Edmund is back! Yes – that Edmund.

I’ve heard it said that the best time to look for a job is when you have one. I think that is utter BS, because it assumes you should be constantly hopping from job to job, maintaining a #Busy status so you can have a lifestyle that impresses people that don’t matter. If you have the wherewithal and financial reserves to #SlowDown and #DoNothingOnPurpose, it’s a big advantage. The introspection alone pays in spades.

I’ve been #FillingMyFishBowl (networking) with #EcosystemBuilders, entrepreneurs, and VC pros intent on #CraftingTheFuture because they believe #ThereHasToBeABetterWay. Along the way I’ve built up a lot of insight into the comfort level and grit needed in #StartupLife. The hardest issue with this transition (luxury goods to tech) has been explaining/translating the skills I gained managing a $MM alcohol business to working in a small startup. I’ve learned some amazing things that I wouldn’t have understood if I still had a full time job. Here’s a list…..


After working remotely (alone, then in small teams), I’m reminded about how much I enjoy working in collaborative teams, especially where transparency, experimentation, and empathy are a part of the #culture. I still enjoy remote work because technology allows us to be just as productive working from a couch – even if your computer is taken over by a Bullmastiff and Maine Coon, who prefer you idle.

What would it take to give this up for an open office plan with foosball and snacks? Alot!


To everything, there is a season – friends, mentors, and even jobs. I never even thought I would ever I quit my last #TourOfDuty, but the universe used some special people, a medical miracle, and the USCIS to send me a profound message: “It’s been a great run Edmund, but you need to #FindYourTribe”. It was very gutsy to quit (some say risky and stupid) in order to #DoThingsThatMatter. It was also scary, but I’ve always been risk-taker who cuts his own path. Honestly, I have no regrets, and if I had a #DoOver, I wouldn’t change a thing. Today, that decision is paying great dividends. In your attempt to #FindYourTribe, you’ve got to be honest in #DefiningYourPriorities and the features of your ideal life (work culture, space, coworkers, etc). You’ve also got to be honestly thankful for the good and bad experiences you had along the way. They all have lessons to impart, but you’ll only learn the lesson when you are truly ready. 


Self-awareness is the ultimate prophylactic (@ScottGalloway’s favorite word next to WOOF and BOOM) in a world that is constantly changing and bombarding you with excessive stimuli. Change is especially good when you know its always a few steps away, even if you are not totally ready for it. If you know who you are, you will rise to the occasion with your highest and best use (skills optimization). In my time off, I was able to break my skull open and pour all my wisdom and experience in a proverbial glass. That was a tall glass of water. I devised an acronym that summarizes my life strategy – #FAIL. FAIL is an acronym for #FillTheGap, #AlwaysAddValue, #Intention, and
#LeverageYourHighest&BestUse. So whether you are:

  • An eager MBA, who wants to “Give people access to the best that life has to offer”;
  • A consummate bus. dev. pro looking to work in SaaS/Fintech startups;
  • An aspiring podcaster interested in the stories of female and underrepresented founders; or
  • An investor with dreams of starting a VC firm focused on #BCorps addressing #ExtinctionLevelEvent problems with consideration for #ESG and #SocialImpact, all you have to do is FAIL – as much as you can. Pun intended.


For the most part, battles are won because one side is technically superior or has a more disciplined approach. However, I think wars are won by teams and people with more #GasInTheTank (grit and determination). Cultivating quality relationships and experiences that give you more situational versatility and mental staying power is the ultimate move to ensure your dreams will be fulfilled. For me, this has translated into a level of comfort with loneliness on the path to success. Whenever it wears me down, I focus on a passage from one of my favorite speeches:

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.

Theodore Roosevelt in “Citizenship In A Republic”; Delivered at the Sorbonne, in Paris, France on 23 April, 1910

#FringesToTheFront #weekendwisdom #storytellers #growthmindset #LifeIsATeamSport #4thofJuly #WOOF #BOOM

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