Tyler Westcott

Have a variety of prospecting techniques, including working with centers of influence consistently over a long period of time.


Tyler N Westcott is the founder of Westcott Financial Partners LLC, an insurance and securities firm in Connecticut. Tyler started in this field in 1999, first as an independent agent selling life and health insurance. After earning his securities license, Tyler joined an established company.

Tyler spent the next several years gaining additional education and licensures to increase his knowledge and provide the best possible service to his clients. In 2018, he began working on building his own firm. His practice now consists of individual and business clients and provides insurance, annuities, and retirement planning.

Where did the idea for Westcott Financial Partners come from?

I wanted to have a simple company name, so tying it to my own name was what made the most sense. We are relaunching our brand new website and should be updated in the next few days.

What does your typical day look like and how do you make it productive?

The priority for my work week is the person-to-person appointments. I keep at least two full office days per week. I try to make at least ten in office per week. I schedule follow up phone call appointments throughout each day, so that will be between ten to twelve of those per day. The basic way to keep my days as productive as possible is to do as much of my case prep in off-business hours. I do my case review, my investment design, and my studying on weekends and before or after work. During the day, I want to be available for my clients and I found this is the best way for me to do that.
Several of my clients are business owners themselves, so I make trips to see them on the days that I am not in the office. I rely on proper scheduling for those days to be productive. I make appointments based on location and will schedule with several clients in the same area to be as efficient as possible with my time and theirs. That way I am not wasting time going from one side of town to the other unnecessarily.

How do you bring ideas to life?

I look at real examples of client stories that have been successful in the past. I will use those past experiences to illustrate examples of potential outcomes, including possible pitfalls and upsides.

What’s one trend that excites you?

I love that the younger generation is really starting to come to the realization that there is a lot of value in working with advisors. They want to be careful with their earnings and plan properly for their future. They are actively seeking that advice more than they have in the past. Another trend I have noticed is baby boomers using a combination of the internet and financial advice as a means of gaining information. They are looking for advice from multiple sources, not just listening to one person. This helps them to be more educated about their finances and to look for the best resources.

What is one habit of yours that makes you more productive as an entrepreneur?

I think my persistence has helped me be more productive. I am empathetic to their needs and what plans they have for their future. This field is one that is constantly evolving and I research as much as possible so that I can stay on top of those changes. I want what is best for my clients, whether it is an individual or a business. I am always evaluating what I can offer that best suits the needs of my clients.

What advice would you give your younger self?

I would tell my younger Tyler Westcott to start earlier in this business and get the education sooner than I did. I feel like I would be farther along in this field had I started earlier.

Tell us something that’s true that almost nobody agrees with you on.

I remember when I was young, my sister got on this kick about eating foods for a long period of time. For some time, she ate as many carrots as she could and after about 90 days, her skin actually turned orange. There is a condition called carrot enemia and it is very real. I’ve told this story a few times over my life and most people think I am making this up, but it does exist.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I schedule personal time for relaxation and exercise. So much of our lives are just work, we need to make sure that we take that time for ourselves. Not having that time will eventually affect your work. Spiritual development and personal development are too important to overlook.

What is one strategy that has helped you grow your business?

Having a variety of prospecting techniques, including working with centers of influence consistently over a long period of time. I have also purchased leads for prospects. I will also introduce myself to perfect strangers and pass out my business cards whenever I can. This strategy still works, I just got a call this week from someone I had given a card to years ago. You never want to rely on just one particular strategy. While it may be a successful one, you could still be missing out on so many other opportunities.

What is one failure you had as an entrepreneur, and how did you overcome it?

I once took on a management and recruiting role and I put a lot of my personal money into that role. It did not turn out as I planned it to. I had to make the decision to not continue that practice. I returned to what I had been doing before and had always worked well for me. Learning from your mistakes is a valuable lesson I think every entrepreneur goes through at some point in their career.

What is one business idea that you’re willing to give away to our readers?

Given that for my clients, I primarily focus in the areas of safe investing and predictable success, I would follow the same strategy when it comes to business advice. The success rate for franchised start ups is anywhere from 4-5 times that of traditional owner start ups. National statistics suggest that less than 20% of non-franchised start ups are still in operation after year 5. According to the SBA loan default rates, the following franchises have the best success rates, Comfort Keepers, Christian Brothers Automotive and Home Instead Senior care to name a few. These default rates are extremely low. I would suggest that if venturing into the world of self employment by a novice business owner a prudent move would be taking a hard look at a franchise opportunity. Franchises such as these have proven models of success built into their everyday business procedures, and the parent franchise company has every franchisees success in their best interest of course. The main drawback of franchise ownership is having to conduct business within the procedures and limitations of the contract with the parent company. I currently work with several franchise owner clients… owners of McDonald’s, Meineke, Subway, Comfort Dental. Several of these clients grew their operations by adding multiple locations under their ownership.

The main thing they have in common is that they all report ease of day to day business operations, ongoing support and advertising from the parent company, and deep discounts on materials/products that they need to run daily operations.

What is the best $100 you recently spent? What and why?

I recently went on a zipline tour. I got to ride one of the highest and fastest ziplines in North America. It was an exhilarating experience where I went about 60 mph around 600 feet above the ground. I can’t really even explain that feeling.

What is one piece of software or a web service that helps you be productive?

We use the Google package, with the calendar and contact management. It’s easy to use across several platforms so it is very helpful. Another really helpful resource I use is called Annuity Rate Watch, which constantly updates annuities and how they have changed.

What is the one book that you recommend our community should read and why?

Ed Slott is considered an IRA and marketing expert. He wrote a book called The Retirement Savings Time Bomb and How to Diffuse It. It has to do with updating tax codes and providing recommendations. It is a step-by-step practical guide to protecting your retirement assets like IRA and 401k accounts.

What is your favorite quote?

I actually have a couple. The first was said by Amelia Earhart, “the most difficult thing is the decision to act, the rest is merely tenacity.” Another one I really love is “There seems to be some perverse human characteristic that likes to make easy things difficult,” and that one is from Warren Buffet.

Key Learnings:

  • Having a variety of prospecting techniques, including working with centers of influence consistently over a long period of time.
  • I think my persistence has helped me be more productive.
  • I am always evaluating what I can offer that best suits the needs of my clients.