Woulda, Coulda, Shoulda

When you see someone who has been where you’re headed, aren’t you curious to know what it was like?  Think about the person hiking up the side of a mountain who has been trekking along for a good amount of time with no real vistas up to that point.  They see hikers headed back down and immediately past pleasantries they ask, “how close am I?!” Or you may bluntly ask, “is it worth it??”  Perhaps you’re exhausted and just want to understand the rest of the terrain, “how’s the rest of the hike?”

It’s natural – we want to benefit from those you have gone before.  Well, you’re in luck – over the next couple of posts, I will share some of the “woulda, coulda, shoulda” words of wisdom from fellow entrepreneurs.  The following are thoughts regarding the structuring of their businesses:

  • “I should have done more due diligence and planning around my first business purchase.”
  • “By not trying to do an add-on acquisition to the engineering company, I was too conservative. We could have grown in other states.”
  • “I should have bought a larger business—$5−10 million in revenue. There is more momentum, more cash for professional management, and it’s just as easy/hard to raise capital for that size of business as it is to raise money for a $1 million business. I think there is more untapped opportunity in the $5−10 million range.”
  • One wishes he had been more daring. “My mistake: not pursuing more ideas and taking them to market.”
  • Another commenter, however, wishes he had stuck to the knitting. “I should have focused more on being the best at our core product, not trying new things.”
  • One of my respondents wishes he’d “paid more attention to maintaining and nurturing client relationships.”
  • “I shouldn’t have let ‘being nice’ and avoiding conflict get in the way of good business results.”
  • Another thinks he knows why his Day of the Wire wasn’t a happy one: “I approached my business as a ‘lifestyle business’ and really didn’t focus directly on growing revenues or growing the value of the organization. Not being an extremely money-motivated person, I lost emotional steam once we were successful and I was able to make a market-rate salary. Employees were happy, customers were happy, cash flow was good. . . . [so] I rested. Eventually, I seemed to lose my drive, as if I thought the challenge was over. When the timing was right to exit the business, I felt like I had less to ‘show’ for all the effort.”

Not all issues and regrets will be the same.  Not all businesses and challenges are the same.  However, the act of starting and growing a business forces an individual to encounter similar obstacles that each must successfully move through.  Learning, understanding, adjusting and adapting are critical to your success.  Use another’s experience to your benefit – let it provide clarity, comfort and validation.  Do even more with the advice from others: overcome challenges more quickly and share your experience with others to help them be more successful.