This past weekend, in between a big leg work out & a delicious cold plunge set at Lifetime Fitness (more on this later), I ran into a former student I had the opportunity of teaching during The Ivey Sales Accelerator Course a few years back. As we got to talking, she asked me what is one piece of advice I would have told myself after during my graduating year at University.

Without a moments hesitation, I said “start a business”.

Taking the chance on yourself to become an entrepreneur in some capacity, whether fractional or full time, gives you skillsets that you can use for the rest of your lifetime.

The first time I did this was in building Canada Beach Soccer-try bootstrapping a beach soccer team and convincing people to invest in a sport that no one understands or believes in (there are beaches in Canada?¿ was the common question). Happy to say we are currently ranked 16th in the world!

You will either fail, and learn a lot about budgeting, cash flow management, forecasting, minimum viable product, sales, marketing, operations etc or you will genuinely make some money, create something of value and maybe sell your business. Either way, you win.

In this weeks edition, we have our very first Guest Writer, my dear friend Scott. Scott and I worked at Salesforce together for a brief period of time and I always loved his hustle, energy and demeanour.

Over the past few months, I’ve been watching Scott build his niche Tech Sales Training business and it’s been a fun journey to watch. The following excerpt from Scott is a good reminder that no matter how complicated the idea is, or how challenging the road ahead, simplicity is sophistication.

1. Why Entrepreneurship with Scott Blostein

2. Industry Updates

3. Upcoming Events

⌛️ Estimated reading time: 4 minutes

There’s a saying that goes, “Everything that’s great is on the other side of fear.”

For years, that phrase echoed in the back of my mind, a quiet reminder of what I could be doing. But like so many people, I was stuck. Stuck in a cycle of comfort, a steady paycheck, and the illusion that someday the “perfect” time to start my entrepreneurial journey would just… arrive.

Spoiler alert: it never does.

After spending a decade at companies like Oracle, Salesforce, Shopify, and ClickUp as a top Sr. Account Executive, I realized something. I was building a dream, but it wasn’t my dream. It was time to change that.

In March 2024, I wrote my resignation letter to ClickUp and post-dated it for July 1st. That gave me a hard deadline. No excuses, no backing out. On July 1st, I was leaving, no matter what, to pursue entrepreneurship.

It was the scariest decision I’d ever made.

The irony? The things that had held me back before: picking the perfect business idea, crafting a clever logo, nailing down a name, all feel so insignificant in hindsight. These were just excuses disguised as “planning.” The real fear wasn’t in choosing a logo; it was in the act of choosing myself.

So where did I start? My coach and mentor gave me clarity:

It hit me like a ton of bricks. Ten years ago, I was in a job I hated, unfulfilled, and feeling invisible compared to my peers.

I didn’t have purpose, status, or a clear path forward. I decided SaaS sales was what interested me, and I came up with a bulletproof plan to land a job with no sales experience into one of the biggest technology companies in the world as a BDR. 

That’s the person I could serve, and that’s who I help coach today, people that are looking to work for competitive companies in technology that are stuck in their current role.

If you’re thinking of starting your own journey, here’s how I’d approach it to remove some of the overwhelming pressure:

1) Start with Service

Forget about fancy branding or registering an LLC. You don’t have a business yet, you have an idea. Your first step is to find people who have a problem you know how to solve and offer to help them for free. You will also make a ton of money finding out how to solve rich people’s problems. 

2) Talk to Your Ideal Customer

Your ideal customer isn’t hiding. Reach out to five people you think you can help, listen to their struggles, and solve their problems. It’s messy and imperfect, but that’s where the magic happens, and you will create a lot of resources you can leverage along the way for future customers. 

3) Earn Testimonials

Those first five people are more than clients, they’re your proof of concept. Their feedback will shape your offering, and their testimonials will make it easier for others to trust you.

4) Improvise, Then Systemize.

In the beginning, everything is trial and error. Don’t rush to automate or build elaborate systems until you know what works. Once you have something that’s repeatable, then you can create structure.

5) Price with Confidence.

When you start charging, remember: there’s no strategic value in being the second cheapest option. Price high, deliver value, and position yourself as the premium solution. Higher prices attract better clients and communicate confidence in your product or service. You become richer. 

From my time in corporate, I learned the power of systems, processes, and frameworks. But as a founder, I realized something just as important:

You don’t need everything figured out to start.

In corporate, perfection is the standard. In entrepreneurship, progress is the standard.

Running a business forces you to ask, What’s the one thing that will move the needle today? That focus is a skill every professional, at any level, can benefit from.

The path to entrepreneurship isn’t linear. It’s not glamorous, and it’s definitely not comfortable. But it’s transformative.

• I learned that your business doesn’t have to be “perfect” to succeed.

• I learned that you need to fail fast in order to find the right opportunity.

• And I learned that you don’t have a fear of failure. You have a fear of what other people will think if you fail. And the reality is, people think more about themselves than they do you.

So, if you’re standing at the edge of your own leap, my advice is simple:

Don’t overthink the jump. Think about the person you were 10 years ago. Could you help them? If the answer is yes, you already have the start of something great.

And remember: the best version of you is on the other side of fear.

Here’s to progress,

~ Scott

📆 EVENTS

📣 Ben Kaplan Book Launch!

📆 January 14th, 2025 7pm

📍 elMoCambo Toronto

Enough said, Get Tickets Here!

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🧘 Longevity

Yes, I decided to hop on the trend and try cold plunging. It was incredible. I did some research beforehand and here are some of the proposed benefits

Proposed Benefits:

#1. Reduced inflammation and swelling: Cold temperatures may cause blood vessels to constrict, which can help limit swelling in strained or injured tissues.

#2. Relief from muscle soreness: Ice baths are believed to lessen delayed onset muscle soreness (DOMS) by reducing tissue damage and inflammatory processes.

What the Research Says:

• Short-term effects: Studies show that cold-water immersion can provide short-term pain relief and a temporary feeling of improved recovery.

• Long-term performance: Some research suggests that routine ice bath use might not necessarily improve long-term training outcomes. Certain studies indicate that while cold therapy may offer relief in the moment, it could blunt the muscle-building adaptations from exercise if used too frequently.

Also, if you read my #ParentGuide newsletter you’ll be happy to know the post India longevity train to India begins.

Have you enjoyed this newsletter? Is it providing value? Do you know somebody that would find it useful? Send them this newsletter and if you refer 5 people your next coffee run will be on me. (5 referrals = $30 Starbucks, 1 Referral = 4$)

As the world becomes more complex, it becomes more and more challenging to stay grounded, focused and aligned. Stay ahead by fostering unity, innovation, and trust across your teams and yourself. Don’t miss out on upcoming events and insights that will help shape your success in the months to come.

- SKV