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Tip of the Spear Ventures

Venture Capital | Private Equity

tip of the spear

9 Lessons In 9 Years at Tip of the Spear Ventures

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February 2012 – I am a 2%’er. Apparently, and I wouldn’t know this until later (much later!) that less than 2% of all entrepreneurial startups achieve successful exit. The experience of raising $8Million, launching a technology software startup that received consumer traction, and having a private equity firm acquire us was incredible! But now what? As I sat on a rock overlooking the ocean in San Diego, CA, I thought back to how it was just 7 years earlier that I had done the same to envision what was to come. “Now what?” was the question I was asking myself again, looking to the horizon where the sky meets the Pacific.

I knew that I enjoyed the private equity experience, and after a few moments determined that was what I wanted to do next. I wasn’t a total stranger to the financial space, having my formal education in Accounting and spending my formative years working in Strategic Planning and Finance. In the 9-years since that day, I’ve built something that I’m very proud of and I’d ike to share with you 9-lessons I’ve learned along the way.

Lesson #1 – Define Your “What?”

What are you made of and what do you offer? This is the “metal” that has been tested at Tip of the Spear everyday. We’ve “pivoted” over the years with different ventures, but the one mainstay was that we are “what” others should desire to be (Namely a group that puts forth A+ effort and content deliverables).

Lesson #2 – More People, More Problems

If you’ve hired as a part of your leadership journey, you know the pitfalls that can come with doing so. We’ve been at different times over the 9-years a small and big organization. I’m happy to say that we’ve settled on a model for the future that includes clustered growth. 

Lesson #3 – Think Strategically, Act Tactfully

In the heat of business, I want to win. I assume you do as well. However, and this was key for me, those “win” moments or victories that I sought to win were often at the expense of the war. I was reminded to think strategically and to act tactfully by an executive coach. The difference in thought/action appears in everything we do now.

Lesson #4 – It’s Lonely at the Top

I originally had a partner at Tip of the Spear Ventures. They were a silent partner that was low on injecting capital, but high on injecting their opinion. At about the three year mark we determined that parting company was best for the company (and us as individuals). I would rather be lonely than miserable.

Lesson #5 – It’s Lonely (but Don’t Go It Alone!)

This piggybacks off of Lesson #4… Even though you’re alone at the leadership helm of your firm/organization, you don’t need to go it alone! While opinions are like you know whats, if you tactfully align with peers/mentors you’ll achieve desired strategic outcomes faster.

Lesson #6 – Change Lives!

Opportunities to make money are everywhere, especially if you look for them! What might be even less obvious is the ability to change lives. I’ve been fortunate to receive recognition that what I was doing was actually making a difference for the people that I worked with. It is simultaneously humbling and rewarding.

Lesson #7 – Time… 

You, me, everyone only has 24-hours in a day. What are you doing with it that maximizes your efforts?

Lesson #8 – Agility

While processes and procedures form the structure of a successful business, the ability to be agile is a key differentiator. Want to stand out from the crowded crowd? Become agile!

Lesson #9 – It takes Blood, Sweat, & Spears!

I sometimes have to pinch myself… I’m a city kid from Detroit that was as my Mother says “Born in the shadow of a Ford manufacturing plant’s smokestack.” How far I’ve come has only been limited by my ability to imagine, visualize, and then take action. At one of our Boot Camps a few years back in Las Vegas, one of the participants accurately summarized that “Success takes blood, sweat, and tears!” The conversation morphed to one of “Blood, Sweat, and Spears!” which has stuck with us ever since (We’re running another Boot Camp starting 2.21.2021 for those seeking Entrepreneurship Through Acquisition). 

SUMMARY

These past 9-years have taught me so much, and I know that the next year will be even more insightful.  I’m determined to further establish in our ninth year the foundation that will drive the firm forward for the next two decades. I recognize that what worked in the past might not necessarily work in the future, so we will have to continue to evolve.  It is my goal to build an institution that outlasts me and continues serving entrepreneurs for generations to come. 

Sam Palazzolo

Business Funding – Subscription Models

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The Point: We’re often asked at Tip of the Spear Ventures, “What are the best ways to go about business funding – Should we consider subscription models?” The short answer is “Yes.” Subscription models are yet another way to accomplish business funding over a traditional capital raise. So in this article we’ll explore business funding through the use of subscription models… Enjoy!

Small business funding refers to the way in which an aspiring or already existing business owner obtains cash to launch a new business, buy an existing business or increase capital to finance future business activity. Business funding can come in many forms, but the most common sources are angel investors, venture capitalists or third party lenders. Entrepreneurs looking for startup capital should take note that all investors are not created equally and each has different goals and business needs. So it begs the question, “Why not explore customer funding options, specifically subscription models?”

Entrepreneurs should consider carefully how they plan to use any business financing options and should always have a game plan before approaching a private investor or a bank. Often it’s the case that entrepreneurs don’t even need to approach an outside funding source. A number of private investors offer startup capital at a discounted rate to entrepreneurial risk candidates who possess a well-developed business plan, a strong personal credit history and a steady track record of profit and loss repayments. To attract and qualify for such financing, entrepreneurs need to demonstrate a strong business plan with a well thought through exit strategy. Additionally, entrepreneurs should develop a set of metrics to track key metrics such as customer satisfaction, profit margins and return on investment.

When it comes to small business funding, entrepreneurs should also keep in mind that there are several options available to them. There are many different types of startup loans including bank loans, credit unions, commercial real estate loans, equity loans from family members and friends, working capital options from multiple lenders and lastly, entrepreneurs can tap prepaid credit cards as working capital. While some entrepreneurs may have better success securing business funding through more traditional means, most borrowers fail to secure enough capital to launch or expand their operations. There are several successful stories of entrepreneurs who obtained small business funding on a shoe string budget. If you have the desire and the ability to be financially secure and succeed in the entrepreneurial business environment, then you may want to consider applying for funding from a private lender. All of this said though, an avenue to pursue before doing so is the applicability of a subscription model as a way of raising capital for your enterprise.

Sam Palazzolo

The Leadership Challenge: Active Listening – 3 Tips!

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The Point: You might be listening, but do you really hear what your stakeholders are saying? At Tip of the Spear we frequently pose this question to the leaders we work with in our Business Advisory Services. The answers we receive are unfortunately shocking (and not in a good way!) Besides, what’s at stake if you don’t listen effectively as a leader? Only everything! So in this post, we set out to explore the leadership challenge of Active Listening and provide 3 tips… Enjoy!

Leadership Challenge Active Listening 3 Tips

Active Listening by Carl Rogers

Active listening or reflective listening was originally defined by noted psychologist Carl R. Rogers. The basics of active listening are to put ones concerns, attitudes and ideas to one-side while listening to others. The theory goes that without these distractions one will be able to observe not only the conscious signals displayed by others, but the unconscious ones as well. Therein you’ll be able to identify the true meaning behind the words that are being spoken.

Typically, active listening is reflected in the following interaction/behavior elements:

  • Providing your undivided attention
  • Encouraging the other party to continue
  • Restarting a potentially stalled conversation
  • Self-disclosing with the desire for reassurance
  • Knowledge improvement, confirmation, and/or correction
  • Connecting the dots in a loosely structured conversation
  • Insight improvement
  • Rapport building

I Listen, Therefore I Hear?

So active listening typically comes down to hearing, and therein a comprehension of what is happening/when. But more importantly than listening is equipping yourself to do something with what you just heard. With that in mind, a robust conversation can take place where ones actions are directly correlated with what was said, including clear comprehension not only of what was discussed, but what next steps will be.

So if so many leaders are listening, why do so many stakeholders feel that they are unheard?

3 Tips for Active Listening

I once participated in a seminar that had quite the magical leader presenting his view on everything active listening. He had three tips that I’ll share with you if you want to become a much more dynamic leader in the active listening space:

Active Listening Tip #3

You must focus intently on the speaker, so much so that you can see the color of their eyes clearly. Why is this important? The leader shared that if they maintained this level of focus, few distractions could interrupt their discussion.

Active Listening Tip #2

Repeat the keywords spoken internally to yourself three times. Why is this important? The leader shared that if he categorized the main topics by repeating them to themselves three times, a virtual card catalog of keywords was created for the conversation. A catalog that could be easily reviewed at a later date when called upon.

Active Listening Tip #1

You have to care. Why is this important? If you don’t care about the other person, the topic their speaking of, or about anything you will never retain anything with the conversation. It sounds simple, but Carl Rogers would have you put your own thoughts/concerns out of the way so as to be fully present in the given conversation.

 

SUMMARY

In this post we’ve explored the leadership challenge of active listening and provided 3 tips to help you as a leader. Most leaders contend that their role as a leader is to provide direction to their stakeholders. In maintaining this “telling” strategy, they rarely focus on the importance of not only what is being said but who is saying it.

 

Sam Palazzolo

PS – If you like this post, I hope you’ll share it with a colleague. I know you’d also like a copy of my latest book, titled “Leading at the Tip of the Spear: The Leader.” In this work I explore the challenges of leading yourself as a leader (and review a roadmap for success). Here’s a link to the book on Amazon: https://www.amazon.com/Leading-Tip-Spear-Sam-Palazzolo/dp/1981860436/ref=sr_1_1?ie=UTF8&qid=1527785570&sr=8-1&keywords=sam+palazzolo+leading

The Leadership Challenge: Competitiveness

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The Point: If nothing truly happens in business until you sell something and the Darwinian principle of “only the strong survive” is alive and well in business today, we scratched our heads here at Tip of the Spear pondering exactly what role individual competitiveness plays across industry. After all, is your ability to compete a signal of success or certain doom/failure in business (and therefore in life)? So in this post, we’ll explore the leadership challenge of competitiveness… Enjoy!

The Leadership Challenge Competitiveness

Is Competitiveness an Economic Model?

Your ability to compete and win in business is a key differentiator for leaders that want to succeed. Have a good idea that you know will be the organization’s next homerun? You’d better be prepared to compete to get it on the agenda for the upcoming leadership meeting. Want to ensure that your monthly goals are met, even though it’s the final week of the month and you’re only 2/3 of the way there? Better fire-up the troops (yourself?) and get those competitive juices flowing STAT!

But what is it all worth, and why exert the effort? After all, aren’t there 12 months in a year (So what if we miss one month’s goals as long as we achieve the annual?) The truth is that while you can’t build a successful leadership career in one-month, the converse relationship of undoing a career can occur in a single moment (NOT the extended timeline of a 30+ day month!)

When it comes to career path success, a leader today will share with you that success can only come through successful competitiveness versus their peers. There are only so many “slots” on the career pyramid at the top to be had. Regardless of the “flatness” of your organization, there are/will always be more people clambering for these leadership roles than there are spots available to house them all. In other words, it’s a matter of economic supply and demand with competitiveness playing the differentiating factor.

Competitiveness Craziness

Amazon reached headline state for all the wrong reasons regarding competitiveness not too long ago. In 2015, the New York Times wrote how workers at Amazon often “complained about 80-hour work weeks, interrupted vacations, coworker sabotage, and little tolerance even for those struggling with life-threatening illnesses or family tragedies.” Worse yet, those that went out on maternity leave were left little time for maternity duties (as work was expected to still maintain a priority, especially seeing how there were countless others more than willing to take the place of those vacating).

Even the Whitehouse has been the subject of competitiveness craziness. Under the Jimmy Carter administration, an edict of spending more time in the evening with family was levied. However, most chose to work late into the evening as opposed to letting peer competitors pass them by in the dog-eat-dog world that is politics.

I’m a Leader… How Do I Become More Competitive?

I worked with a client that had a “Want to Move Up? Screw Up!” policy whereby in order to achieve a promotion, the leader would have to essentially make a mistake (potentially costing the organizations hundreds of thousands of dollars!) The organizational leaders questioned competitiveness, and instead rewarded those that in their eyes “put themselves out there for the sake of innovation where others did not.” With organizational politics at fever-pitch levels, what then is the poor high-potential future leader to do?

SUMMARY

It’s important to know the culture of the organization at which you are competing. Know that organizational leaders reward the “bowl people over” theory of competitiveness? Begin bowling others over for success! See that “slow and steady wins the race” at your firm? Then curtail competiveness (but still ensure that you end up in the winner’s circle at the end of the race!) There simply is no “One Size Fits All” rule here when it comes to competitiveness, but culture identification is key to success.

 

Sam Palazzolo

 

PS – If you enjoyed this post on the leadership challenge of competitiveness, then I know you’ll enjoy my new book, “Leading at the Tip of the Spear: The Leader” It’s filled with antidotes to allow you to succeed on your leadership journey. Click the hyperlink above (or here: www.LeadingattheTipoftheSpear.com)

 

The Leadership Challenge: Executive Vocabulary – 3 Tips

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The Point: At Tip of the Spear, we’re “lucky” to get exposure to a lot of leaders. Each of these leaders has their own unique way of speaking, and let’s face it, some speak better than others! With a wide-range of personalities, backgrounds, and goals, each executive seems to bring their own sometimes-unique vocabulary to the table. It is this executive vocabulary that sometimes (perhaps every time!), makes us not hear the message they are attempting to deliver. We started thinking, what role does executive vocabulary play in an organization’s success and is there anything a leader can do to enhance their opportunities? So in this post, we’ll explore the leadership challenge of executive vocabulary and provide 3 tips… Enjoy!

The Leadership Challenge Executive Vocabulary 3 Tips

I Can’t Believe What I Just Heard!

“Say what?” we heard a leader exclaim. Not the most outrageous statement we’ve ever heard, clear of vulgarity, and just intriguing enough to make us pay attention to what was to be said next. But it was exactly what was said next that had us scratching our Private Equity | Venture Capital heads! You see, the leader went on to use an executive vocabulary that would have been more appropriate on an MTV-episode instead of the boardroom where we were being pitched to invest in their company.

Just what about using slang/vulgarity is appropriate for executive vocabulary? While some would argue that there certainly is passion at work, is this passion in a desire for performance the most appropriate display of the effort/energy required to have to resort to gutter-speak (or the sewer)? So why do we do it (and we’re all guilty of it every once in a while, right?) The answer seems to lie in either laziness of lack of vocabulary!

3 Tips to offset the Leadership Challenge: Executive Vocabulary

So what follows is our attempt to help you, the leader, offset the leadership challenge of executive vocabulary (In other words, you might be lazy from here forward, but will not resort to inappropriate language due to lack of vocabulary or a strategy to employee that vocabulary!):

Executive Vocabulary Tip #3 – Learn the Right Words

There are over 150,000 words in the English Dictionary (and throw on top the 50,000+ words in the Urban Dictionary and you have a disaster brewing!) What do executives and master communicators do so as to offset the poor choices associated with the leadership challenge of executive vocabulary? They learn the right words that are powerful and practical in use so as to communicate better.

Executive Vocabulary Tip #2 – Learn the Right Way to use the Right Words

What’s at stake if you don’t improve your executive vocabulary? After all, it’s a choice you can make that will determine your career progression. Excellence can be had by ensuring that the right word is at the ready so that you can always communicate your ideas clearly and succinctly with impact. Also, sounding intelligent is important! So make certain you know how to use each word in the proper context.

Executive Vocabulary Tip #1 – Use the Right Words the Right Way in the Right Context

So how do you put executive vocabulary together for a winning strategy, so that you can start receiving those promotions you so rightly deserve and/or ensure that those you lead actually follow? Simple: Learn executive vocabulary constantly. There never is a bad moment to learn a new word for proper utilization!

SUMMARY

In this post we’ve explored the leadership challenge of executive vocabulary, along with 3 tips. Employing a much better vocabulary as an executive is not optional (it’s mandatory!) Empower yourself with an executive vocabulary so that you know the words that can propel your career trajectory onward/upward!

 

Sam Palazzolo

PS – I just published my 4th book, aptly titled “Leading at the Tip of the Spear: The Leader” which looks at the skills needed to successfully lead in today’s business climate. I hope you’ll purchase a few copies for yourself/the leaders you know. 100% of the net profits go towards supporting my 501(c)(3) charity at the Javelin Institute. Amazon’s editors had the following to say about the work:

“In these days when so many expect so much recognition for doing so little, leadership seems easy, when it’s really harder than ever. To be that person who truly takes a chance, makes a stand, and ventures out in front of the crowd requires courage, commitment, and conviction—qualities that more than ever seem to be in short supply. There’s no shortcut to the skills that mark a true leader, but there are definite strategies that can help you set your internal compass, find the right route, and steer others onto the right path.

Leading at the Tip of the Spear – The Leader focuses on the physical, mental, emotional, intuitional, and spiritual abilities that are found in leaders who are willing to lead. You will learn to develop your individual values and purpose, strengthen your foresight and failure-resistance, step up your self-control, plan for any contingencies, and always stay on the offense. It will take effort and energy to understand the proposed process and fully implement it in life and business, but leadership is all about doing hard things for the right reasons. Once you’ve mastered true leadership, nothing can stop you from having the career and the life you’ve worked for.”