The Kickass Entrepreneur
  • About
  • Blog
    • All Blogs
    • Create Wealth (Investing)
    • Entrepreneur Interviews
    • Featured Top Posts
    • Growing Profits
    • Growing Revenues
    • Marketing
    • Positive State of Mind
    • Real Estate Investing
    • Retirement
    • Sales
    • Selling your Business
  • Book
  • Courses
  • Podcast
  • Resources
  • Contact
The Kickass Entrepreneur
Subscribe
The Kickass Entrepreneur
  • About
  • Blog
    • All Blogs
    • Create Wealth (Investing)
    • Entrepreneur Interviews
    • Featured Top Posts
    • Growing Profits
    • Growing Revenues
    • Marketing
    • Positive State of Mind
    • Real Estate Investing
    • Retirement
    • Sales
    • Selling your Business
  • Book
  • Courses
  • Podcast
  • Resources
  • Contact
  • Retirement

My Three Year Semi-Retirement Winter 2021 Check-in

  • January 2, 2021
  • 4.2K views
  • 6 minute read
  • Jeff Wiener
Entrepreneur Semi-Retirement
Share
Tweet
Share

Remember me?

Yes, it’s been a while since you’ve heard from me.

I haven’t written a blog post since September – that’s almost four months of not connecting.

So what happened?

I started a business.

My 2020 Year in Review

In early September, a friend of mine invited me to speak with a private equity investor about investing in her fund.

She outlined their investment pipeline, their process for deal review, expected returns, and overall investment philosophy.

At the conclusion of the call, I wondered why I was going to invest in someone else’s fund when I believed I could do a better job of building my own fund.

And so that’s what I did.

In early September 2020, I laid the groundwork for what would become my next venture, and that’s what I started a few days later.

When I sold my last business in 2017, I decided that I never wanted to own or run a business, ever again. I had decided that from that point forward, I was going to be an investor, but, I didn’t want to take the lead on running a business.

But then, Covid happened.

In 2019, I was away from my home for at least 5 months of the year, and frankly, running a business was the furthest thing from my mind.

Fast forward to this past fall, and with no in-person meetings, restaurants, flights, or travel, I was finding myself at a desk for way too much time.

Then, and at the same time, I divested the balance of my shares in the telecom company I sold in 2017, stepped down from the board, and had both extra cash, and time as a result.

The confluence of those factors, mostly as a result of Covid, led me to begin what would be my next challenge.

If You’re Handed Lemons, Make Lemonade:  My Private Equity Fund

Running a business wasn’t in my short, or frankly, long-term game plan.

I didn’t want to manage staff and didn’t want the responsibility of overseeing another business.  BUT, I was lacking a challenge.

So I’ve given myself one year to build a new business, and more importantly, put the management team into place so that by the time we can travel once again, I would be ready to hand the reins to the team to manage the entirety of the business leaving me to focus on strategy and direction.

And so, CloudStrike Ventures was born, and with it, my first employee and first acquisition.

What is CloudStrike Ventures?

Over the course of the last couple of years, I’ve developed a skill in SEO, and website monetization.

So with my tactical skills of SEO, SEM, marketing, and monetization in hand, and my strategic skills in building and managing a team, I made my first acquisition.

My first acquisition, which is a small business website, cost $70,000 and had a historical two-year track record of consistent traffic and profit of about $2,800 per month (approx. $34,000 per year) for a 25X monthly multiple. The acquisition seems like a no-brainer considering the 50% YoY return, and in the last 3 months, we’ve nearly doubled the revenues which make the ROI even better.

I’ve since made three more acquisitions, all of which have similar returns, and now have a team of five people including an operations manager, SEO specialist, content writer, web developer, and an admin person starting next week. You can visit the website for CloudStrike here.

I expect that over the course of the next six months I will make another six to ten acquisitions, and expand the team accordingly.

Website Assets: The Next Major Asset Class

I’ve written extensively about real estate for the last two years, in particular, multi-unit-residential (MUR).  You can download a FREE copy of my book here. and I’ve also written about how an investor can make a 110% IRR inside of two-years in MUR real estate,

One of the challenges with real estate is that CAP rates are trading at historically low multiples approaching 3% or lower in many North American cities.  At those levels, real estate, and MUR specifically, is a more challenging long-term play at the moment, and it is for those reasons that I am looking at alternate asset classes.  Digital assets, buying and monetizing websites, offer the best returns I’ve seen in a long time.

My only challenge now is that I have to build a team.

The Power of the Remote Team

The interesting thing about this business is that there is no office, frankly, we don’t even have a phone number, and while I have to be careful not to say the word “never”, I don’t expect that I will ever open an office. All of our team members work remotely.

It isn’t just my team that’s working remotely. Many businesses around the world have been forced into a work-from-home mode, and with that, comes the realization that if you’re going to hire someone to fill a role, that individual doesn’t have to be in the same city, or, frankly, even in the same country as you or your business.

My focus at the moment is hiring the best people to do their respective roles and putting the processes in place so that I can step away from the tactical side of the business by fall 2021.

My initial investments are going quite well.  

So far we are achieving a 100% IRR, and I expect that rate of return to continue for the next three years.

*** if you want some clues on how I’m achieving those types of returns, you can read this article:  How to Make a 600% Return on a Business Investment Inside 24-Months

Best of all, I am enjoying the process of building a new business, especially considering I am stuck at a desk for the foreseeable future.

The Non-Work Side of My Life

My wife and I were fortunate to have our two kids home for the holidays. They’re both doing well – my daughter is in university, and my son graduated from university last spring, and is now gainfully employed as a software developer.

We’re spending a lot of time indoors, and considering my aversion to cold weather and snow, I bought a treadmill, rowing machine, and have built a small gym in my house. 

We’re hunkering down, keeping a safe social distance from our friends, and making our way through the cold Canadian winter.

My Investments

My portfolio has done quite well in 2020 up almost 10% for the year, which is excellent considering my targeted return of 5%. I haven’t taken any outsized risks, and am still very conservatively invested, although I did buy some bitcoin, gold, and more tech stocks during the spring of 2020 which definitely helped drive much of those returns.

2021 and the Next Year

Between Covid, the up and down of the financial markets, the state of many small businesses including restaurants, and anything in the travel and hospitality space, the challenging job market, the psychological toll that isolation has had on many, and the heated state of political affairs in the US, 2020 likely won’t go down in the history books as a banner year.

Remember though that every cloud has a silver lining, and when the world hands you lemons, you can still make lemonade.

I still do believe that now is the best time in the last 30-years, maybe even longer, to start a business.

We’re at the precipice of many generational changes that are all happening at the same time including health, financial, and political. There hasn’t been a time in my lifetime, where I’ve recognized so many opportunities.

If you’re stuck in a job that you can stand, working for a crappy boss, then find another job, or, start a new business. Stop making excuses.  Stop saying the words “I can’t”, and start saying “I can”.

Start dreaming of your ideal future, and go achieve your dreams.

When you say the words “I CAN”, your subconscious will then take that as a command. You will be programming your subconscious and will begin the path toward your future success.

Make 2021 your year to accomplish your dreams.  Write them down, both short and long term, and then focus your energies on accomplishing them.

Good luck, and stay healthy

And by the way, if this is your first time here, you can read my backstory here.

Thank you for your interest in THE KICKASS ENTREPRENEUR'S GUIDE TO INVESTING. Three Simple Steps to Build Massive Wealth with your Business's Profits. Please check your email to confirm the book download. Form: 400529

There was an error submitting your subscription. Please try again.

Related Posts:

  • Semi-Retired at 50. An Entrepreneur's Life Post Business Sale. My Summer…
  • My Journey Post Business Sale as I Sail Into a New Harbour. The Next Stage,…
  • Just Days From Running Out of Cash, Stressed, and in Therapy, to an 18%…
  • Best Retirement Calculator For Retirement Planning
  • 7 Key Tips to Prepare Your Business for Winter Storms
  • Winter Is Coming: Learn How To Drive In Snow Like A Pro
Share
Tweet
Share
Jeff Wiener

Jeff sold his company to private equity in 2017 and is now semi-retired. Jeff spends time traveling and with his family, writing this blog, managing his real estate portfolio of apartment buildings,  overseeing his investment portfolio, investigating angel investments, coaching other entrepreneurs, and managing his private equity holdings. Jeff is currently on a couple of boards, one for profit, the other not for profit, and now helps entrepreneurs grow their business, profits, and ultimately, create wealth.

Previous Article
remote leader
  • Growing Revenues

Things That Remote Leaders Should Keep in Mind

  • January 1, 2021
  • Monica Serreon
View Post
Next Article
marketing strategy
  • All Blogs

4 Ways To Create A Marketing Strategy For Student Small Business

  • January 4, 2021
  • Monica Serreon
View Post
You May Also Like
Retired Early
View Post
  • All Blogs
  • Retirement

How to Retire Early. Here’s How Much You’ll Need and How To Get There

  • September 9, 2022
  • Jeff Wiener
passive income
View Post
  • Create Wealth (Investing)
  • Retirement

Building Wealth Through Passive Income and Business Ownership

  • December 29, 2021
  • Jeff Wiener
Entrepreneur Semi-Retirement
View Post
  • Featured Top Posts
  • Retirement
  • Selling your Business

My Journey Post Business Sale as I Sail Into a New Harbour. The Next Stage, Entrepreneur Semi-Retirement, and Life Post Business Sale

  • December 14, 2021
  • Jeff Wiener
Semi retired at 50
View Post
  • Retirement

Semi-Retired at 50. An Entrepreneur’s Life Post Business Sale. My Summer 2020 Check-In

  • June 27, 2020
  • Jeff Wiener
Early Retirement
View Post
  • All Blogs
  • Retirement

Semi-Retired at 50, Traveling, and Enjoying Life. My Winter 2020 Check-In

  • December 12, 2019
  • Jeff Wiener
Jeff Wiener Semi-Retirement Update
View Post
  • All Blogs
  • Retirement

Entrepreneur Semi-Retirement. The Life of a Semi-Retired Entrepreneur [Summer 2019]

  • July 16, 2019
  • Jeff Wiener
Jeff Wiener, Semi-Retirement
View Post
  • All Blogs
  • Retirement
  • Selling your Business

My Eleven-Week Experience Running a Business as Interim President. Semi-Retirement on Hold!

  • June 18, 2019
  • Jeff Wiener
View Post
  • All Blogs
  • Retirement

Another Chance at Bat As I Step Back Into a Management Role.

  • April 2, 2019
  • Jeff Wiener

Join 6,472 Entrepreneurs That Get My Business Building and Wealth Creation Posts by Email

I can teach you how to build a successful, profitable business, and turn that into millions in personal wealth.

Thank you for your interest in THE KICKASS ENTREPRENEUR'S GUIDE TO INVESTING. Three Simple Steps to Build Massive Wealth with your Business's Profits. Please check your email to confirm the book download. Form: 400529

There was an error submitting your subscription. Please try again.

We won’t send you spam. Unsubscribe at any time.

Recent Posts
  • Logistics Software 1
    Accelerating Your Business Growth: The Role of Logistics Software Development
    • March 20, 2023
  • crude oil 2
    Energy Futures: What to expect in 2023
    • March 17, 2023
  • man writing on board 3
    What is the Difference: Lead Scoring vs. Nurturing
    • March 17, 2023
  • group session 4
    Managing Wealth: 4 Reasons You Need to Opt for a Money Management Company
    • March 17, 2023
  • BUSINESS 5
    Planning to Start a New Business Abroad? These 11 Tips Might Help!
    • March 16, 2023
Featured Posts
  • Become a Decamillionaire
    How to Become a Decamillionaire, Grow your Net Worth to $10 Million, and Join the 1% Club
  • how to become wealthy
    The Entrepreneur’s Secret to How to Become Wealthy and Build a Personal Fortune
  • Most Profitable Small Businesses
    27 of the Most Profitable Small Businesses to Open in 2023
Categories
  • All Blogs (1,034)
  • Business (220)
  • Canadian Financial Products (4)
  • Create Wealth (Investing) (131)
  • Entrepreneur Interviews (25)
  • Featured Post for Main Menu (4)
  • Featured Top Posts (23)
  • Finance (55)
  • Financial and Investment Calculators and Economic Data (114)
  • Fitness (5)
  • Growing Profits (72)
  • Growing Revenues (115)
  • Growing Revenues (70)
  • Marketing (139)
  • Millionaire and Business owner interviews (3)
  • Positive State of Mind (68)
  • Real Estate Investing (17)
  • Retirement (13)
  • Reviews (12)
  • Sales (15)
  • Sell Me This Pen (8)
  • Selling your Business (13)
  • Starting a Business (1)
  • Startup Ideas (14)
  • Technology (112)
  • Top Products (4)
  • Uncategorized (54)
Follow us
Author
Jeff Wiener
Jeff sold his company to private equity in 2017 and is now semi-retired. Jeff spends time…

    CHECK OUT MY BLOG, AND SUBSCRIBE

    about
    The Kickass Entrepreneur

    Expand Your Business, Improve Profits, Create Wealth

    Expand your business, improve your profits, and create wealth. Each one of the three can be elusive goals. Follow the right steps, and you, too, can create financial independence. It is possible … you just have to take the right steps.
    NAVIGATION
    • About
    • Blog
      • All Blogs
      • Create Wealth (Investing)
      • Entrepreneur Interviews
      • Featured Top Posts
      • Growing Profits
      • Growing Revenues
      • Marketing
      • Positive State of Mind
      • Real Estate Investing
      • Retirement
      • Sales
      • Selling your Business
    • Book
    • Courses
    • Podcast
    • Resources
    • Contact
    TAGS
    apartment BATNA Business business failure business growth business sale Capitalization Rate CAP Rate cash cash flow Creating Wealth Discipline entrepreneur entrepreneurship excel extra cash Featured goal setting Growing Business investing investment real estate M&A marketing Marketing KPIs Mergers and Acquisitions | M&A | Entrepreneur Blog Millionaire millionaire next door mistakes MUR Peter Principle Profit profitability real estate retirement revenue Revenues sales sales management Semi-Retirement Blog | Entrepreneur Blog | Small Business Blog small business Stagnant stocks success Thomas Stanley wealth
    RECENT ARTICLES
    • crude oil
      Energy Futures: What to expect in 2023
      • March 17, 2023
    • deck of folders with insurance word on it
      Tips for choosing the right auto insurance coverage
      • February 17, 2023
    • holding laptop
      Tackling pros and cons of virtual reality tours when buying and selling houses
      • February 9, 2023
    • Rising gold prices concept. Investment in precious metals in the stock market
      The Pros And Cons Of Investing In Precious Metals
      • February 9, 2023
    • man looking at his tablet
      These Are The 7 Mistakes Six-Figure Earners Make
      • January 7, 2023
    • starting your own business
      6 Must-Know Tips For Starting Your Own Business
      • January 1, 2023
    The Kickass Entrepreneur
    • Coaching
    • Book
    • Blog
    • Contact
    • Privacy Policy
    • Terms
    • Disclaimer
    • Facebook
    • LinkedIn

    Input your search keywords and press Enter.