Interested in starting your own entrepreneurial journey in consultancy but unsure what to expect? Then read up on our interview with Aaron Tilley, Founder and CEO of Æsir Insurance Services, located in Dallas, TX, USA.

What's your business, and who are your customers?

We are an insurance agency providing outsourced underwriting for various commercial casualty lines. Our customers are Fortune 1,000 businesses, but equally important are the commercial brokers who distribute this business. Providing excellent service to both policyholders and brokers, along with creative risk solutions and deal structuring, which, in turn, facilitates pricing flexibility, is the key to ensuring their support.

Tell us about yourself

I'm an attorney by training and have over 20 years in international business and commercial insurance. I've founded, co-founded, or advised on a total of four start-ups as and led a successful turnaround. I "grew up" at an insurer that started in '85 in a hotel room and is now one of the biggest in the world, which inspired me to do the same, particularly as many of the early employees were still there during my tenure.

I spent years targeting my career towards entrepreneurship by rotating through key operating disciplines in my area, earning professional designations, volunteering in industry groups, and networking. I'm pursuing this path to see what I can accomplish without any artificial limitations, and now that I'm on it, I am motivated by the fear of failure. The dichotomy between optimistic assertiveness and terror is the yin and yang of early-stage entrepreneurship.

What's your biggest accomplishment as a business owner?

It's a tie between surviving multiple years and one pivot required by the failure of key third parties to deliver on their responsibilities and securing the support of distinguished industry veterans to serve on my Board or otherwise support the business.

What's one of the hardest things that come with being a business owner?

Uncertainty. You plan the best you can for as many potential outcomes as you can envision, but it is impossible to escape a high degree of uncertainty with respect to your financial condition, execution, reliability of key service providers, etc., which requires you to be a solid risk manager in addition to your many other roles.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Ensure a stable starting position. This includes both finances and your personal relationships. Entrepreneurship can exact a heavy toll on both.   The better positioned you are with respect to your personal finances, the better you can whether the launch period where you may pay out money with nothing coming in. The better communication you have with your significant other, both upfront and during the first few years, the better you can manage the relationship stress. High tolerance for pressure is a must.
  2. Methodically plan everything before you begin. If you can create your company on paper with a corresponding budget, it makes it much easier to execute and gain the support of others. Maximize your revenue streams and keep costs to a minimum until you can afford them to ensure you are using resources to their peak efficiency. Feed those parts of the plan with the best chance of success and starve the ones that are high cost, high touch, or slow growth until later phases.
    Seek constructive criticism and be prepared for multiple versions as you refine your ideas. The better you plan before you put yourself at risk, the less risk is in general. You absolutely will face the questions you ask yourself (and likely others). Anticipating those and answering them before they are asked establishes credibility with your audience, be it prospective employees, investors, or other gatekeepers. Be realistic about costs, timing, and success rates which will all break against you more often than not.
    Read Built to Last as you go along and build your clock. Plan for the time when you will have to make a choice between taking third-party funding in exchange for equity and possibly the loss of control versus maintaining independence and bootstrapping your organization. There are plenty of articles on how you can be rich vs. being king that can provide food for thought, but know when and on what terms you're prepared to make these trades. As your plan executes, be prepared to pivot when you run into obstacles.
    Lastly, have objective indicators that will signal that it's time to move on because the plan hasn't worked, and know that, if that happens, you can move on with your head held high and no regrets – then do everything possible to avoid those indicators becoming a reality.
  3. Build your team to fill gaps in your own expertise and empower them. It doesn't matter if you are multi-talented; having a diverse team of experienced individuals with enough gray hair supporting your plan is invaluable and lends instant credibility to your efforts, and can help you avoid stepping on rakes.

Is there anything else you'd like to share?

Dark days as an entrepreneur are unavoidable. Know yourself and whether you can handle them, and then put yourself in the best position to survive them financially, emotionally, and professionally. Identify your problems and map out possible solutions. Remember that almost failed. Remember who supported you during this time, who vanished, who threw rocks and treated them accordingly.

Lastly, take some time periodically to disconnect and take a breath with your family and friends. Stay positive and mentally flexible. Find a few trusted confidants and make use of them. Celebrate your little successes along the way and those who helped you achieve them.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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