Pearls of Wisdom From Bootstrapping Entrepreneurs

Diving deep for the perfect entrepreneurial metaphor, the founders of Bennu, Blurts, GetMinders, and OpenInvo are growing gems under intense pressure.

On the orders of Spain’s Queen Isabella to bring back riches,
Christopher Columbus set out for uncharted waters in 1492. While
discovering vast new lands assured his place in posterity, Columbus’s
real triumph was uncovering vast beds of oyster pearls off the coast of
Venezuela, a rare natural gem that the queen coveted beyond all else.
The “pearl rush” that Columbus started way back when is not unlike the
rush to entrepreneurship underway today, a surprising outcome in a
challenging time.


And more to the point, the beloved pearl provides a lustrous metaphor
for the joys and pressures of entrepreneurship, something I’ve discovered
personally and as a result of recent interviews with the founders of
four start-ups. Though each of the entrepreneurs I interviewed offered
pearls of wisdoms worthy of an entire article (see the complete
interviews here
), this provides a deeper dive into the collective
mindset of entrepreneurs, especially the type of founder that is
prepared to bootstrap their company from inception to market

It takes an irritant to get started


While the proverbial “grain of sand” is a myth according to
, it does take “an irritating microscopic object [to become]
trapped within the mollusk’s mantle folds” for a pearl to get started. For entrepreneurs, the irritant can be as simple as
personality type. According to Emily Lutzker, the founder of
OpenInvo, an innovative resource for idea generators, “I only had
one ‘real job’ once and was told I was disruptive in the workplace,”
thus necessitating her entrepreneurial journey.


Sometimes the irritant hits the founder personally. Ashok Kamal,
founder of Bennu, explained that, “like any
good business, the idea behind Bennu was born out of a problem–the
obscene amount of garbage being dumped into landfills.” Jeff Stier, got
the idea for the voice tagging utility called Blurts after a
voice message from his daughter was annoyingly and irretrievably
deleted. And Jesse Middleton, founder of GetMinders, a service that
reminds people when to take their medicines, got the idea when thinking
about his grandfather who has Parkinson’s and the toll it was taking on
him and his family.

Growth usually requires outside help

It was the rarity of natural pearls that made Columbus’s discovery so
important in the 15th Century. Today, more than 99% of the pearls sold
are the result of human intervention through a 20th Century process
known as cultivation. Not surprisingly, entrepreneurs are almost always
dependent on the help of outside resources, both in terms of capital
and expertise. What is surprising is how many boot-strappers find those
resources close to home from friends and family. Noted a grateful
Lutzker, “I didn’t ask for money, [friends and family] volunteered.”


Outside help also comes in the form of advisers who can add layers of
experience. Offered Bennu’s Kamal “You can avoid a lot of unnecessary
mistakes by establishing an advisory board from the outset.” “It’s easy
to neglect this task in favor of immediate concerns but once we
recruited seasoned and candid advisors, Bennu become much more efficient
and productive,” added Kamal. In Jesse Middleton’s case the critical
advice was more home grown, as his “wife gave [him] a kick in the ass to
really get the ball rolling!”

Success has its own measurement scale

As long-time leaders in the pearl trade and the first to patent a
cultivation process, the Japanese also established the unique weight
measurement scale for pearls known as momme. For modern day
entrepreneurs, measures of success tend toward the benevolent, hoping
that their products and services make the world a better place.
Explained Lutzker, “I’m a bit of an idealist and I want to live in a
world that fosters and rewards things that make us human and celebrates
our differences.” Added Middleton, “getting our product in the hands of
millions that need to remember to take their medicines would be pretty
amazing for us.”


Many entrepreneurs share the ability to see beyond the making of
their first “pearl,” measuring success in terms of helping others grow
their own. Offered Kamal, “I hope the business will outgrow its
founders so at that point, personal success would mean being in a
position to help aspiring entrepreneurs to achieve their dreams.”
Similarly, Middleton noted, “I’d like make it to a point where I can
invest in other’s ideas that can make the world a better place.” Added
Lutzker, laced with the irony that bedevils boot-strappers, “I’d like to
think that success is still a starting point, not only a result.”

You still have to beat the odds

Naturally occurring pearls of a decent size are literally one in
million. Columbus and Co had to harvest hundreds
upon hundreds of oysters in the West Indies just to find a single pearl
worthy of their faire queen. So it is with start-ups, hundreds are
conceived while few achieve notable success. Beating these odds takes
an indomitable spirit. Explained Stier, “if you’re not passionate and
pigheaded about what you believe in even when everyone is a naysayer,
you’ll never get it done.”


Kamal took this a step further, suggesting that entrepreneurs needed
to be more than thick-shelled, “I’d subject the [would be entrepreneur]
to a psychological exam to ensure that they are just crazy enough to
start business.” Acknowledging the ups and downs, comes with the
territory. Noted a cash-challenged Stier, “the depressing moments have
to be outweighed by the moments of joy, like knowing we’ve birthed
something from our mind that other people are talking about.” Concluded
an undaunted Lutzker, “Yeah, sure I knew it would be hard–when are
worthwhile things not hard?”

Final Note: In the interest of full disclosure, I became a bit of a
pearl diver myself when I agreed to help Jeff Stier with the launch of For you angel investors out there, I’ve recorded this
Blurts for you
Click on the following links for the
complete interviews with Lutzker, Kamal, Middleton, and Stier.


About the author

Drew is the founder of Renegade, the NYC-based social media and marketing agency that helps inspired B2B and B2C clients cut through all the nonsense to deliver genuine business growth. A frequent speaker at ad industry events, Drew’s been a featured expert on ABC’s Nightline and CNBC