Startup Elation and Pain: 11 Life Lessons Learned the hard way

From Bucket Buddies Founder. From the head and heart.

I’ve been putting this off for some time now. I never had a problem saying “farewell” until now. It’s time to put Bucket Buddies into hibernation. The end of the runway has arrived. We got off the ground a few times but could not make it soar. Losing the engine, our lead developer, grounded us and we are unable to execute. It is gutting to miss out on ‘product market fit’. But we are not alone. Bigger and smarter startups tried and failed. Many more are doing similar things in this space. Someone will make it stick.

I find benefit in every experience through learning, reflecting on the good and bad. Here are some favourite lessons learned the hard way. Sprinkled with websites well worth exploring. Countless times I thought to myself: “I wish I knew that earlier.” If you’re curious, about startup soft skills, hard business, kittens or life, read on.

1. Start with the WHY. Always.

Understanding motivations is fascinatingly powerful and more than a life’s work in itself. Your motivation to build. Their motivation to act. Fear? Love? Sex?! Be the kid asking “why? why? why? why? why?” Pick from any number of delicious paradigms, Maslow’s needs to Behavioural Economics and beyond.

Maslow’s hierarchy of basic human needs. Updated 2015.

Our motivation varies by person & over time. Intrinsic motivation from within will trump external motivation. How can you help them look good, feel good, do good, belong or follow the herd? Which incentives incite: recognition; money; connections? What defines ‘them’ as a group? Your team? Your market?

Recommended gurus: Simon Sinek and Nir Eyal

[How did we do? Could do better]

2. Team is everything.

Then execution. The rest is noise. Ideas are meaningless without execution.

Recruit on cultural fit first. Skills are learnt. Experience gained. But.. Would you want to spend a pressure cooker week locked in a bunker with your colleagues?

How to determine this? Evaluate your company values, translate that into behaviours and ask questions about candidates their actions & behaviour to find matches. e.g. “What do you do for fun?” “What makes you uncomfortable?” More examples, including the very Good website.

First find complementary personalities, then look for complementary skills. We had the Hacker Hustler Hipster triumvirate of tech startup skills, but perhaps needed more diversity in personality types.

I believe everyone can do what they love. Facilitate this, and you’re on the way to self-organising, self-motivated teams. Work should give energy, not toil and trouble. Outsource if it costs you energy. Find no joy in blogging, accounting or coding? Find someone who does. [How did we do? We did the right things and I’m proud of the team and culture we built, but ultimately the team didn’t stick. A fundamental reason why we Failed. Could do better]

3. Overcome the fear of failure.

Then fail fast. Fail cheap. What’s the worst that could happen? You have to get a different job?

Founding a startup is the hardest thing I have done, by a long stretch. Imagine mooorrrrphing into a baby octopus, teething your new tentacles, learning your first, simultaneous, high-stakes poker hands.. in a blizzard.

To put this in perspective, for years my last corporate boss repeated that I had ‘the hardest job in the company.’ 60,000 employees and I’m the dumb one trying to move mountains from a million miles away. I say this not to blow my own trumpet, but to illustrate that entrepreneurship without a safety net is orders of magnitude harder than intrapreneurship in a cosy corporate cocoon. Failure is likely.

So what!?

My ultimate goal was always learning, and I have loved everything I have learned. [Pass]

Of course Bucket Buddies dreamt of helping millions reach their dreams, we still do. [Fail]

Does writing this article feel like catharsis? No. Happiness, yes. I am a disciple of happiness. At the end of the day, a spluttering startup was not making me happy. I started with an unwavering belief that this was certain to work. The more I tested and learned, the more I grappled with uncertainty. So:

4. Get to product market fit as soon as humanly possible. [A never ending journey and our biggest Fail].

Whether it’s a new corporate geography or innovative startup: Show me the money.

When building a community, you must choose:

A. The Purists option, our choice, to focus on community first and the money will follow.

B. The Practical option and monetise from the getgo.

We had good indicators. Users told us we solved problems for them and they wanted to refer us. Yay! We’ll grow virally! I still have an itch to scratch. We validated that others users share this itch. But, like other competitors (Everest with $2.5m funding, 43 things with 3million users), we could not shoehorn this into a sustainable business. I always saw ways to improve on competition (more social! fun! easier! prettier! addictive!) — but is it orders of magnitude better? How good does the solution need to be to reach sustainability? Is the concept something people need rather than want? Are you a painkiller or vitamin?

Don’t be a solution looking for a problem. Don’t get attached to the idea, get attached to the problem to solve.

5. Validate assumptions.

We became Lean disciples. The Lean Startup is the best business book I have read. External validation (eg competition in the market) can be counter-intuitive. Just because competitors are growing and funded, don’t assume they are sustainable.

Make data-driven decisions. Sure, trust your intuition. But if you want rational people to follow, you had better prove it. Then explain why.

Everything can be quantified… even abstract concepts such as emotion and sentiment. Quantify writing? Sure: grammar errors; sentence complexity; shares; likes. If you can measure it, you can manage it. Visibility is the first step to empowering better decisions. Measure the right things, mind. Pirate metrics aarrr great. [Could do better.]

6. Customer development never stops.

Active listening is so powerful. I loved learning that everyone is lying. Eye opener: we all lie about our intentions. Even to ourselves. Yes I like your idea! Sure I’ll pay for it if you build it! … Bollocks! Researching users’ future intentions is meaningless. Uncover facts. Past behaviour, not future. Don’t base decisions on future intentions. Replace “Do you like this?” & “Are you interested to buy this?” with “What did you do/pay to solve this problem?” & “Click to buy now”

Postpone judgement and don’t force your solution onto a problem.

[We learnt the hard way. Could do better]

7. Velocity is vital.

Mixing part-time and full-time team founders can hurt. One leg moving faster than the other. Address each individual’s motivation continuously.

Nurture every nugget of momentum, celebrate every little win together. And hold each other accountable. Helps if you have a whip-cracker in the team. Trello boards and kanban process were our weapons of mass construction. These tools make a huge difference to any Project management.

Rhythm rocks. It’s the heartbeat that gets everyone jumping, reaching in unison. We wanted to introduce Scrum, but failed miserably once our product engineer quit. [Could do better.]

Timing is everything. You don’t necessarily want to be the first to broach that golden egg market, especially if it’s NEW. But don’t be the last to the party, scrambling for bits of identity in a ferocious frying pan of competition. Whilst we’re talking tictock time, worship this simple rule for timeline expectations: Double everything. Then DOUBLE AGAIN!

Maybe the secret sauce for startup success here is lots of cash, PR, or an external trigger to reduce the barriers. Precursors to Facebook & Google failed because the market & ecosystem was not ready. No use inventing Netflix if bandwidths can’t cope with video streaming.

8. Working remotely sucked eventually for me and made it exponentially harder for us.

Why? Solitude and speed issues. Side by side, synced up and in the same room as your core team means you can execute at speed. Momentum motivates and creates a virtuous cycle. Stagnant stop-go does not.

Solutions for solitude: HOffice. Search for local co-working spaces. Some are even free! And never eat alone.

We all need a significant number of strong relationships. Familiarity and frequent favours, reciprocated, drives this.

Solutions for connectivity: If you can’t be in the same room, video hangouts beats phone beats chat beats email. Slack to rule them all.

I’m an advocate of working from home 2-ish days a week: freedom; eco and timesaving benefits. Be sure the team schedules overlapping hours.

With unpaid part-timers and virtually unpaid full timers, you had better sell the vision and KEEP SELLING IT. An approaching light at the end of the tunnel motivates. Darkness does not. Keep the light visible at all times eg pic embodying the mission on walls or on desks.

[Could do better]

Focus on the light

9. Focus.

We had 23 scaling frameworks and 12 revenue streams to test. Can’t do em all, gotta prioritise. There are a bewildering number of avenues to explore. Evaluation and communication of the one thing that will move the company forward is critical. Make sure everyone knows what the long term big picture is PLUS what’s most important right now. We had plenty of structure eg simple templates like this. [Pass, could do better]

10. Know yourself.

What is your deepest Motivation? Strengths, weaknesses? Tests like MBTI, Enneagram and BOSI are fun places to start the journey of exploration. All are complimentary and complementary. I know I get immense value from other people. Stuck in my office, in my head, was not giving me enough of the gold-dust I get from strong relationships: interaction; a mirror; value; banter. Where do you get value from? If ‘others’ features anywhere, and it does for 67% of us, be aware of the dangers of introspection and get social juice from somewhere, hub, family. [Pass] Or better still, flip your value system from extrinsic to intrinsic. Somehow?!?

Meditation is part of my journey, or more importantly, mindfulness. I would not want to push it on anyone, as I felt it was first pushed on me by giddy fairy preachers. I finally bowed to the volume of respected voices raving about its metamorphic potential. This now resonates:

I’m forever fixing in my head, analysing or planning. How can I free the mind & body for the present? After all, it’s a gift (image). Dip your toe in with Headspace or Happier courses. This will help you manage yourself first. Your energy.

How can you help others if you are not aware / can’t help yourself? Find the times in the day/week/year to optimise activity around your circadian cycle and life rhythms. Then be aware of the effects of the entrepreneurial ride: The Rollercoaster. From the soaring thrill of seeing folks sign up en masse, the adrenaline of winning an award, through suffering sudden founder splits. Crippling. And the constant drip-drip of resources, energy, money, time, precious like your last water through parched fingers. Constantly licking your fingers for a morsel of moisture is exhausting. Find ways to replenish, to carry you through anything.

On the ground, the last kick in the guts was being tantalised, teased, then missing out on a €150k grant by a whisker. Figure out ways to deal with the highs and lows. Who can you count on to keep you grounded or lift you up? How can you improve your mood, just by 5%, one step at a time? Quit or quit griping. Make your own luck. [Pass & fail. Could do better]

11. Focus on the frikkin feeling! EMOTE, people!

Tools are great, but it’s the human side that is most important. Did you know there are 50% more ‘feelers’ than rational ‘thinkers’? Sure, trust your data. But if you want emotional people to follow, you had better embody it. When people make decisions, their feelings are maybe twice as important as any factual argument. Inspiring extreme emotions is the goal of great storytelling, positive or negative.

Apply this to any aspect of business you can. Especially marketing, mission statement, branding, company name, website, advertising.. Tie every public word, image and colour back to an emotion. But also recruiting & culture building. We validated our ability to attract great talent — team, advisors, contributors. As a founder, you are the biggest asset of the company. [Pass]

So. My utmost respect and awe to all entrepreneurs out there, striving, struggling or succeeding. Success takes a special blend of skills and guts, market and team conditions.. and LUCK Entrepreneurs will save the world! We salute you.

Hopefully, you know most of these lessons. I went in knowing we had no choice but to take the harder routes (remote, PT & FT founders). I thought we could be the beat the odds. Stack the odds in your favour.

I could go on for days! I do write primarily for myself but I love to help. But wait, let’s first test if there is an appetite. Validate that assumption. Let me know if this content is helpful by commenting and sharing. More depth to come on the above, business development & sales, entrepreneurship, productivity & wellbeing, self-awareness, tools & templates. Our favourite resources: coming soon…? Over to you.

Huge THANKYOU hugs and hits from the hip flask go to the multitude of contributors and proper-uppers: Team, family, THNK, Startup Weekend team, Google, Neyenrode, Katie and other social psychologists research friends, Nick Robinson, Mark Turrell, Startup Next team, Douwe, Kulin, Michiel, Arjan, Marc, Brant, Mike, Sandra, Spif, Brian, Paul, Cristina and many more……..

With all my heart: Cheers!


Originally published at on July 12, 2015.