Entrepreneurs Must Kick Down The Door When Opportunity Knocks

Because Your Big Break May Start As A Little One

This article originally appeared on Forbes HERE.

Ever heard of the band “Five Cool What?” No? I am not surprised. When opportunity knocked, rather than busting open the door, they first asked, “What do you want?”

In 1987 the band was discovered by Ron Fair, a rising executive at Chrysalis Records. Ron brought the band into Chrysalis’ headquarters and introduced them to his staff. According to one of the band members, “They were swooning over us.”

Once the tour concluded, the group returned to Ron’s office where he notified them that he would initially sign them to a development deal. He made it clear that this approach would allow the band to re-cut a few of their demos, which he would use to persuade the label to sign the band to a full-fledged recording contract.

Without consulting anyone else in the group, one of the members leaned forward and dramatically delivered a line that would haunt each band member for the remainder of their musical careers, “Ron. That deal sounds like a field goal. We’re looking for a touchdown.” Not surprisingly, Five Cool What never spoke with Ron again and failed to score a safety, let alone a touchdown.

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There are a number of entrepreneurial lessons which can be drawn from Five Cool What’s naive mishandling of their potentially big break.

Self-awareness – As discussed in Your Greatest Ability Is Often Your Availability, entrepreneurs who are self-aware and not self-absorbed are better equipped to identify potential opportunities. The band’s inflated self-importance clouded their ability to properly vet Ron’s proposal.

Attitude – During the early stages of their careers, emerging entrepreneurs must conform to their customers’ realities. The band failed to realize that Ron was their customer. They misconstrued Ron’s polite, VIP treatment and failed to realize they had not earned his deference.

Before the “field goal” comment was uttered, Ron’s reality was that he was offering to help shape the image and sound of a clueless band, in order to increase the chances that they would be signed to his label. After his offer was rejected, Ron’s perception was that the band was too high-maintenance and immature; the least desirable combination of the four employee archetypes described in No One Is Irreplaceable.

Small World – Every industry is small. Industry veterans know each other and freely share information about up-and-coming products, companies and people. Work hard to ensure that trusted opinion leaders say positive things about you and your startup.

It is unclear if Ron ever shared his opinion of Five Cool What with other music insiders. However, if he did, it assuredly would not have been complimentary.

Bad Audible – Even though the other band members were appalled when the “field goal” comment was made, none of them spoke out. This lack of unanimity could have been avoided if they had planned their responses to potential scenarios in advance.

Your startup cannot similarly allow a sole member to perform strategic planning on the fly.

Homework – The band did not fully appreciate Ron’s ability to change the trajectory of their career. If they had realized the scope of his influence, they would have welcomed and appreciated his mentorship. A bit of up-front research would have served the band well.

Level Playing Field – The band entered the meeting with Ron ignorant and alone. Although it would have been awkward to have a lawyer in tow when Ron made his offer, they could have asked for time to contemplate the offer. Five Cool What might have been comfortable saying “Yes” to the development deal, if they had discussed the offer with a trusted, experienced advisor. Unfortunately, they had no such resource on their startup team.

Ron Kills It While The Band Is Killed

Unlike Five Cool What, Ron’s career prospered. After leaving Chrysalis, Ron eventually became Chairman of Geffen Records, after being nominated for six Grammy Awards (four of which he won). Some of the contemporary artists he helped develop include: Black Eyed Peas, Pink, Lil’ Kim, Christina Aguilera and Lady Gaga.

The Five Cool What band member who declared a field goal unacceptable was kicked out of the group shortly after the unfortunate encounter with Ron.

Soon after the incident, the band changed its name to The Tearaways and under their new moniker, they enjoyed some modest success.

During my brief tenure as the band’s bumbling manager, their song Jessica Something was selected by Rhino Records’ for inclusion on Power Pop Classics of the 90’s, alongside Matthew Sweet, Jellyfish, The Rembrandts, The Posies and The Lemonheads. The liner notes stated that although The Tearaways were, “One of the more obscure acts on this compilation,” they remain, “a band eminently worthy of the widest possible attention.” Their GoToMyPC radio jingle remains one of my all-time favorite one-minute songs.

As noted in The (Non)Sense Of Entitlement, talent is only one factor that impacts an entrepreneur’s success. Emerging entrepreneurs must have the humble tenacity required to make chicken salad out of chicken $hit.

Even though a development deal was not Five Cool What’s ultimate goal, it was an appropriate first-step, which a more mature band would have gladly accepted. Given that few people were ever exposed to the band, their name was ironically appropriate.

Be sure your company does not become the entrepreneurial equivalent of a great band that few people have heard. Incremental success is the norm. Thus, it’s OK if your startup has to settle for a few field goals as a prelude to its end zone dance.

You can follow my startup-oriented Twitter feed here: @johngreathouse. I promise to never Tweet about sunsets, puppies or that killer burrito I just ate.

John Greathouse

John Greathouse is a Partner at Rincon Venture Partners, a venture capital firm investing in early stage, web-based businesses. Previously, John co-founded RevUpNet, a performance-based online marketing agency sold to Coull. During the prior twenty years, he held senior executive positions with several successful startups, spearheading transactions that generated more than $350 million of shareholder value, including an IPO and a multi-hundred-million-dollar acquisition.

John is a CPA and holds an M.B.A. from the Wharton School. He is a member of the University of California at Santa Barbara’s Faculty where he teaches several entrepreneurial courses.

Note: All of my advice in this blog is that of a layman. I am not a lawyer and I never played one on TV. You should always assess the veracity of any third-party advice that might have far-reaching implications (be it legal, accounting, personnel, tax or otherwise) with your trusted professional of choice.

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  • I agree it’s important to stay humble, but I have seen on more than one occasion investors taking advantage of inexperienced entrepreneurs.  At the end of the day, it’s all about making the best decisions with the available information and not looking back (although learning from mistakes IS important, and learning from others’ mistakes equally so).  Thanks for sharing this story!

  • John Greathouse

    Alex – do not confuse being humble with being a pushover. Any investor who attempts to take advantage of a less experienced entrepreneur should be called out. The Funded and similar sites give entrepreneurs a voice.

    Continued best of luck to you and thanks for your feedback.

  • Kalleschurtz

    You got the Title wrong….., You meant to say that ” Entrepreneurs Must NOT Kick Down The Door When Opportunity Knocks”  otherwise your Story does not make any sense.., They actually DID knock down the Door, with them asking for a Touchdown. Or let’s say, offered a Finger and took the whole Hand… That was Bold and admirable. They were knocking down the Door, just like in your original title. If you analyze the story further, It was Ron, who was the Douche, not being consultative enough, mature enough, to recognize a good Mentoring opportunity with this Band.
    His arrogance and need to be “courted” and treated with respect and accomplishment, was immature for that situation, He got very lucky, that the Band had no other success after his turn, otherwise he would have been burned. If Ron was as great as his shadow, he would have laughed at that comment, and mentored the Band, and told them where they were currently standing, and where they needed to grow into. He did none of that, instead had a alluric Hissy Fit and walked away in arrogance. 

  • John Greathouse

    Kalleschurtz – You raise some interesting points. In the title, I meant that entrepreneurs can’t even wait to politely open the door, but they must “kick it open.” However, I do see how this can be confusing. I used a less colorful title when I published this on Forbes.

    Re Ron, he certainly could have been more nurturing. One could argue that if Brian Epstein had acted this way, The Beatles would have never made it out of the Cavern. However, the music industry isn’t generally known as having a collaborative culture. I am sure Ron felt that he would be better off working with bands that gladly accepted his help, rather than asked for something better.  

    Thanks for adding your thoughts and sharing another side of the debate.

Follow John’s Startup Oriented Twitter Stream!


Follow John’s Startup Oriented Twitter Stream. He promises to never Tweet about sunsets, kittens or awesome burritos.

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