Words Matter Less

Everyone is familiar with the concept of the proverbial "shit sandwich."

If you have to deliver bad news, how you frame it makes all the difference. The message itself is only part of the equation. The delivery is what determines whether someone actually hears you.

Mom Knew Best

There's a reason these lessons stick with us from childhood.

Our moms weren't just teaching manners. They were teaching us about building real connections with people.

The same words can land completely differently depending on tone, timing, and context.

Final Thoughts

The takeaway here is simple: what you say matters, but how you say it matters more.

Whether you're delivering tough feedback, sharing difficult news, or just trying to get your point across, remember the sugar that helps the medicine go down.

This is one of those timeless communication principles that applies everywhere. In business, in relationships, in everyday conversations. Master your delivery and your message will actually land.

Next time you need to have a difficult conversation, think about how mom would tell you to say it.

Three Indicators

If you're hiring for a sales role, the three best indicators someone will be successful seem to be:

• High agency
• Attractive woman
• Low rejection sensitivity

Balancing Traits

It's interesting to note that the second and third traits often balance each other out. This creates a unique dynamic where the ideal candidate possesses a specific combination of characteristics. Consider this: often, attractiveness can inadvertently increase rejection sensitivity due to heightened social awareness or fear of negative judgment. However, finding someone who has overcome a past struggle with their appearance can lead to a powerful resilience and drive.

The Sweet Spot

So, if you can find an attractive woman who used to be ugly or fat, that’s your sales closer. This background can be a powerful predictor of success. Overcoming those challenges may help create a strong sense of self and drive to prove themselves. If you are rethinking risk management on your sales team, consider these indicators.

Conclusion

In summary, the three core traits to look for in a sales candidate are high agency, attractiveness, and low rejection sensitivity. The ideal candidate might be an attractive woman who has overcome past insecurities about her appearance, as this combination often results in a resilient and driven salesperson.

These qualities, when combined, create a powerful force in sales. Seeking out individuals who embody these traits can significantly improve your team's performance and drive your business forward.

Start prioritizing these indicators and see the difference it makes.

If you’re not sure, ask your broker now before they leave for the weekend. You want to be quick to report any losses because carriers will likely be inundated with calls & emails in a widespread event.

Building Prep

Some high level interior & exterior building prep tips that may be useful to implement and/or to share with employees and/or tenants in advance of a storm:

• Seal windows and doors
• Display signs warning of icy conditions
• Keep walkways, driveways, parking lots, doorways, etc clear of ice & snow
• Position snow blowers, generators, heaters, etc ready for use
• Monitor all walkways and stairs for safety
• Post security or block off unsafe areas so no one enters
• Check vacant buildings or spaces to ensure heat is on and reduce likelihood of pipe rupture
• If carbon monoxide alarms sound or if there is a smell of gas, leave premises & evacuate tenants immediately
• Monitor for danger of collapse due to snow or ice and evacuate as necessary

Final Thoughts

In summary, preparing in advance for severe weather and reporting losses quickly can help minimize damage and ensure a smoother recovery. Also, implementing building prep tips and sharing them with employees can make a big difference.

Taking these precautions protects your assets and the safety of everyone involved. It’s a proactive approach to managing risk and ensuring business continuity.

Everyone stay safe & warm!

1/1/26 reinsurance renewals brought generally good news for insureds. 2026 represents the sharpest decline in risk adjusted global Property insurance rates since 2014.

Buyer's Market

Property insurance remains in a 'buyer's market', characterized by competitive pricing, eased capacity, and average 10%–20% rate reductions in Property lines.

Driven by record capital and strong returns, the market saw increased competition and stabilized conditions, though some tightening remained in casualty sectors. This was specifically in the US and for more challenging sectors like construction and real estate, particularly multi family real estate where casualty claims are most challenging. Understanding commercial insurance trends can help you navigate these shifts effectively.

Renewal Details

Here are some details on 1/1/26 reinsurance renewals:

• Property reinsurance rates fell by 10%-20% due to abundant capacity outpacing demand. The market shift focused on pricing, attachment points, and coverage.
• Increased capacity led to accelerated market softening across many lines, driven largely by strong reinsurer returns (estimated at 17.6% ROE for 2025).
• Dedicated reinsurance capital grew by 9% in 2025. Stronger supply dynamics and high capital levels intensified competition.
• 2025 insured Catastrophe losses were lower than expected, approximately 18% below the five-year average.
• Casualty renewals experienced slightly improved conditions over 2025 with generally stable capacity, though some markets are still focused on lackluster performance and long-tail loss concerns.

Market Outlook

Overall, this is mostly positive signals through at least the first half of 2026. Insurers are positioned to leverage these reinsurance conditions to restructure programs and see a continuation of rate reductions occurring in 2025 on Property insurance.

Your Business

So what does this mean for your business? Now is the time to leverage positive market conditions and restructure programs to be competitive before the next hard market hits.

It's easy to sit back in a soft market and enjoy easy, incremental rate reductions. This is exactly how so many people found themselves unprepared for rate increases in 2021-2024. Exploring alternative risk financing strategies could help you stay ahead of market cycles.

This is not the time to be complacent. Insurance will continue to be a key component and set apart the most competitive operators from the average operator.

Conclusion

If you're not utilizing a competitive insurance program to reduce OpEx and increase NOI on CRE portfolios, you will be outperformed by peers who are. This will be catastrophic as the market likely begins to harden again in 2027 and beyond.

Insurance is not the sexiest way to value engineer, but it is one of the most consistently reliable.

Take advantage of these favorable market conditions now. Review your current insurance program, restructure where possible, and position your portfolio for success before the market shifts again.

The article covers how creators in the CRE space are shifting from traditional word of mouth to digital word of mouth by sharing insights, teaching basic concepts and showing up consistently online.

One part of the piece highlights my approach:

Influencers who stand out are ones who share basic concepts of the business and can communicate them simply, said Skylar Romines, a commercial real estate insurance broker and founder of ATW Advisors. Romines has almost 10,000 followers on LinkedIn and 24,000 on X. Romines said it’s just a digital attempt to boost the very traditional word of mouth. Turning clicks to cash? More commercial real estate influencers take a stab at it – By Brannon Boswell

I also shared how I tailor content by platform, simplify core ideas and rely on consistency to build momentum over time.

If you want to read the full story, including insights from other CRE creators and industry leaders, click here.

Instead of addressing real economic problems, we told them to stop buying avocado toast and make coffee at home.

The Dismissal

We got here by telling young people they are stupid and lazy and should eat less avocado toast or make coffee at home instead of looking at real, valid complaints about the current economic system that exists largely in part due to skewed dynamics created to support boomers at the detriment of the younger generations.

Real Struggles

People who have to finance basic necessities and cannot pay off student loans or afford homes until they are 40 and older, rightfully feel like they have been abandoned by the economic system they are supposed to be a part of.

This is not entitlement.

This is a legitimate crisis.

Course Correction

If we do not want millennials and younger generations to continue skewing socialist, we need to take these issues seriously and course-correct so that young people have viable futures in this country.

The outcome will not be good if this continues to be ignored.

We are getting just a small glimpse into it with New York City now.

Who Got It

No one understood this problem better or spoke about it more vocally than Charlie Kirk.

Yes, I realize I have been nuanced and honest enough here to adequately anger both sides of the political spectrum, but this is real.

Conclusion

Young people have legitimate economic grievances that demand serious attention and policy changes.

Ignoring these issues will only push more people toward radical alternatives and create deeper societal fractures.

If you like my content, follow me on X and LinkedIn for more.

After speaking on a panel about navigating drama and protecting mental health online, the timing felt almost too perfect given recent events.

If you find yourself doom scrolling or feeling angry, sad, or drained after time online, these strategies can help you regain control.

Track Your Time

Pay attention to your create versus consume time. This is the number one metric to track for healthy social media use.

Social platforms are not inherently good or bad – they’re just tools. Make sure you’re using them and they’re not using you.

Touch Grass

If you find yourself feeling heavy after time online, shut the devices down. Take 30 minutes or an hour for a walk in nature.

This simple reset can completely shift your mental state and perspective.

Connect IRL

Call a friend and talk on the phone or go meet up in person. Humans were not designed to process so much information so quickly, especially negative or complex information.

Real connections help counterbalance digital overwhelm.

It’s Parsley

Here’s a concept worth stealing from Bob Knakal: people who are being nasty online or spewing negativity are like parsley on your dinner plate. Don’t pay attention to it. Toss it aside and focus on the main course.

Conclusion

Everything is a choice. You can choose to set boundaries and protect yourself from digital drama and negativity.

Here are the key strategies to remember:

• Track your create versus consume time ratio
• Take breaks in nature when feeling overwhelmed
• Connect with friends through calls or in-person meetups
• Treat online negativity like parsley – ignore it and focus on what matters

Your time and energy are your most valuable assets.

Choose to invest them wisely by taking control of your social media experience rather than letting it control you.

Follow me on Instagram, LinkedIn, X, or Patron View to read more insights like this, or click here to read more articles on my blog.

I shared insights about doom scrolling and protecting mental health online, covering the same strategies detailed in my recent article about doom scrolling. The timing felt perfect given current events and the need for these conversations.

Key Insights

During the panel, I emphasized the importance of being mindful about our information consumption.

“Think about your information diet. I don’t think as humans we were meant to take in this much negative information all the time,”

The session covered four main strategies for protecting mental health online: tracking your create versus consume time ratio, taking breaks in nature, connecting with people in real life, and treating online negativity like parsley on your dinner plate that you simply toss aside.

Audience Feedback

The panel received positive response from attendees.

One participant shared their thoughts online:

“I am pretty drama free and didn’t think I’d get much out of this. Was wrong, great session.”

This feedback highlights how even those who consider themselves relatively unaffected by social media drama can benefit from intentional strategies for managing their digital consumption and mental health.

Photos from the Event

Here are a few photos from the summit.

Conclusion

The Mind Over Media panel at CREI Summit demonstrated the growing need for conversations about digital wellness and mental health.

Here are the main takeaways from the session:

• Be intentional about your information diet and consumption habits
• Recognize that humans weren’t designed to process constant negative information
• Implement practical strategies like the create versus consume ratio
• Take regular breaks in nature and prioritize real-life connections

The positive audience response shows that people are ready for practical solutions to manage their relationship with social media, which connects to the power of asking for help and protect their mental well-being.

Follow me on Instagram, LinkedIn, X, and Patron View for more updates like this.

Everything took off faster than I planned, and it quickly became clear I was just a vessel for something much bigger than myself.

I explore this further in The Power of Asking.

In this article is the story to how I started running my business, and the lessons I learned.

Life Before

A year ago, I had good money, job security, and a nice life in an industry that had always supported me. But I couldn’t shake the feeling that something was off, even though plenty of people told me I should just be grateful.

Then I heard Sahil Bloom say something that hit home:

The worst thing isn’t failing at your dream, it’s living out someone else’s dream well.

That’s exactly where I was.

Always Ready

The first lesson I learned? Don’t convince yourself there’s a right time or that you can prepare for everything.

You need to be prepared, but also be prepared to feel unprepared. That’s okay and it’s part of the process. You’ll never feel completely ready, so don’t wait for that moment to come.

Bootstrap Smart

Here’s something that might surprise you: you don’t need to accept money or take on investors right away, especially for a service business. I started ATW with less than $5,000 in total startup costs, including insurance, website, state filings, and QuickBooks. Keeping overhead as low as possible was key because it absolutely can be done.

One of my biggest surprises was how many people offered money when I said I was starting a business. Be ready for this and know what direction you want to take. We probably could have grown faster with outside capital, but I didn’t want to be responsible for other people’s money before proving it was viable. Plus, doing things organically gave me space to implement systems without total chaos.

Do Everything

This next reality check was harder than expected. In the beginning before you have employees, you’re doing everything. Full stop.

If you’re leaving corporate to start a business, this likely means doing tasks you’ve had someone else handle for years.

I hadn’t fully thought this through, so be ready for it.

Outsource Strategically

As things start moving, you’ll want to start outsourcing what makes sense before hiring full-time employees. I knew things like a bookkeeper were necessary from day one, and I’m glad I spent the money. It’s not something I’m good at, and I would have wasted too much time trying to do it myself.

A lot of people suggest admin and scheduling help, but that doesn’t take much of my time or brainpower, so I kept doing it myself. The key is figuring out what makes sense for your specific situation and skills.

Ask Everything

Don’t be afraid to reach out for help. I contacted so many people in the week between deciding to quit and launching ATW. Yes, it was just a week because I had to move quickly. If I gave myself six months to think about it, it never would have happened.

Most people want to help, especially entrepreneurs who want to help new entrepreneurs. You’ll get more support than you expect if you just let yourself be open to receiving it.

Conclusion

The next chapter looks like continuing to grow, making a few more hires in 2026, and starting the process of me stepping back from running everything day to day. This is my biggest challenge, so feel free to hold me accountable.

Looking back at this year, here are the key lessons I learned:

• Don’t wait for the perfect time – be prepared to feel unprepared
• You can start a service business with less than $5,000 in startup costs
• Be ready to do everything yourself in the beginning
• Outsource strategically based on your skills and time constraints
• Ask for help – entrepreneurs want to support other entrepreneurs
• You’re probably more prepared than you think

I had no idea what to expect when I started, but everything so far has been better than I ever imagined. I would never suggest anyone take advice from me, and I often advise against it. But there’s a good chance something amazing is waiting for you on the other side of whatever is stopping you.

Ready to make your move? Stop waiting for the perfect moment and start preparing for the imperfect but exciting journey ahead.

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Follow me on Instagram, LinkedIn, X, and Patron View to read more insights like this, or click here to read more articles on my blog.

The level of “it’s so over” sentiment in the timeline is higher than I’ve ever seen.

Usually, you can go outside and find that real-life friends are talking about different things, but this time, most people seem a little nervous in person too.

Even if not nervous, they’re definitely talking about what’s happening.

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The Economic LandscapeReclaiming American DynamismThe Challenge of UnityTime for Reflection

The Economic Landscape

I’m not a macroeconomic expert, so I’ll say little about tariffs.

My sense is this strategy works to redistribute wealth to younger and less wealthy people on a medium to long-term timescale and will come with short-term pain—BUT that’s not really what this article is about.

This is about a nation divided.

Reclaiming American Dynamism

Nearshoring or re-shoring is a great idea in a lot of ways. Most of us intrinsically know we’re not the country we used to be.

We miss American dynamism.

We know we have it in us to be the greatest country on earth, but we haven’t been showing up or performing our best.

Frankly, we can’t get our act together long enough to work out a long-term plan. Bringing manufacturing back to the US in any meaningful way requires a decade or more of planning and execution.

The Challenge of Unity

If we could work as a unified team and agree on a path to put America first in a meaningful way—and follow through on that plan—it’s likely the best long-term strategy.

Our over-reliance on foreign nations has been problematic for decades and is worsening. It makes sense to lay that foundation before implementing something like the current tariff strategy.

But we can’t. We’re subject to brutally tribalistic elections every four years.

Instead of focusing on building a future, too many people spend their days arguing about men in women’s sports, which politician had sex with whom outside of their marriage, who’s a Nazi this week, and what books should be in schools.

We can’t see the forest for the trees.

Time for Reflection

“United we stand, divided we fall” isn’t just a proverb—it’s a parable. And we’re living it out in real time.

It feels like an ideal moment for reflection—both self-reflection and a broader contemplation of what we’ve become as a society.

We’ll be back stronger if we can figure out how to work together again.

CREi Movement

This marks the third annual list from the CREi Summit, recognizing women leaders who are making significant impacts in the commercial real estate industry.

The honorees were selected by a team from CREi Movement led by Alison Beddard, based on industry influence and social media presence.

Skylar Romines, Founder of ATW Advisors, had this to say,

“Always nice to see women in the CRE space. Solid list and thanks for including me.”

The CREi Summit emphasizes the importance of diverse perspectives in commercial real estate, with their annual list highlighting women who are driving change and inspiring others through their leadership.

Skylar Romines has established herself as a thought leader in commercial real estate and insurance through her advocacy for business owners and transparent insurance practices.

As the founder of ATW Advisors, she has pioneered an independent approach to insurance and risk management that gives clients more control over their insurance programs and better terms.

Her strategic negotiation skills and deep industry knowledge have made her a powerful advocate for businesses navigating the complex world of risk management.

For more information about the summit and the complete list of influential women, visit CREi Summit.

Here are a few women who were named on the list:

Amy, Ashley D’etta and Dianne were all named

Anne, Elisa, Elke, and Marissa were also featured

Della, Alison, Carrie, and Stephanie were also included

About ATW Advisors

ATW Advisors is an independent risk advisory and owner’s insurance representation firm dedicated to making insurance procurement transparent.

The company supports business owners by providing expert negotiation services with insurance brokers, carriers, lenders, and other stakeholders.

ATW Advisors handles the complexities of insurance, so clients can focus on their core business operations. The firm is built on a foundation of transparency, integrity, and client advocacy.

About CREi Movement

The CREi Movement is dedicated to advancing the commercial real estate industry through innovation, education, and fostering diverse leadership.

Their annual summit and recognition programs highlight excellence and forward-thinking approaches within the industry.

This is your ‘walking around’ coverage.

Related: Alternative Risk Financing for Family Offices.

Testing at a vacant site? Due diligence is required.

Looking at a new building? Due diligence is required.

The Risk

If you fall through a roof while inspecting a building, you won’t be covered for third-party property damage or injury unless your General Liability policy includes due diligence coverage.

This is especially ugly if you have a policy where coverage is only applicable to specified locations.

What To Do

Please talk to your broker or insurance team about this if you haven’t.

The policies are usually cheap (could be $2.5k-$5k minimum premium in many cases) or the exposure can sometimes be added to an existing GL policy (more likely for construction GL than operational GL).

Yes, some of these things (like site testing) can also be addressed contractually through indemnification, but that’s another discussion.

However you structure it, just make sure you have DD coverage.

Here are some of the trends and changes that I found interesting.

For more on this topic, see General Liability Insurance in 2025.

I explore this further in Alternative Risk Financing for Family Offices.

Reinsurance and Premium Trends

Reinsurance indicators continue to play out on renewals.

Property insurance premiums for most CRE portfolios are decreasing.

General liability premiums are increasing, often by double digits percentages, at renewal.

General Liability Coverage Changes

Whilst General Liability is an overall small % of premiums for many CRE owners, carriers are also continuing to have increased underwriting scrutiny and reductions in coverage.

Some of these reductions in coverage are significant and can have a material impact in potential balance sheet risk from uncovered claims.

Some examples to look out for:

• A&B exclusions
• A&M exclusions
• Firearms exclusions
• Animal liability exclusions

These exclusions are most commonly impacting multifamily owners but can be an issue for other asset classes as well.

Warehouse and Industrial Asset Approach

There continues to be a bifurcation in how underwriters approach warehouse and industrial assets, with a strong focus on tenancy and public exposure (e.g., a manufacturing facility vs. a trampoline park).

International Market Engagement

On larger portfolios, London & Bermuda are attaching to lower towers than we’ve seen in the past.

Data Quality and Risk Assessment

Data availability and quality will continue to be a critical differentiator in outcomes.

Best in class operators (from an underwriting/RM perspective) are adding detail to SOVs.

Beyond standard information like most recent update years for major building systems (wiring, HVAC, roofing, plumbing), detail like type of wiring, type of electrical panel, and type of roof materials are becoming more important.

Carriers and brokers are continuing to utilize more risk analytics and location specific analytics to assess potential risk.

Potential high risk factors like wildfire score & crime score are location linked vs. based on a general area or zip code, etc.

Conclusion

‘The story’ is more important than ever.

At scale, capacity re-entering the property market gives some relief.

However, the ability to articulate how one operator approaches capex, risk mitigation, and other factors compared to peers is still leading to differentiated outcomes.

Follow me on LinkedIn for more content like this!

Here’s how asking for what you want can transform your life in ways you never imagined.

The Social Media Sprint

Building a digital presence isn’t just about numbers – it’s about creating genuine connections from scratch.

When you start with zero and commit to authentic engagement, every connection becomes a stepping stone to something bigger.

In just 18 months:

• LinkedIn: 0 to 7,300 connections
• Twitter/X: 0 to 13,400 followers

Lesson: Every meaningful network starts at zero. Your late start is only permanent if you never begin.

The Speaking Circuit

The microphone feels heavy until you realize your voice carries weight.

A simple goal of one speaking engagement per month turned into:

• 14 podcast appearances
• 3 conference speaking roles
• Future booking for Personal Branding conference

Lesson: When you voice your ambitions, the universe has a funny way of exceeding your expectations.

The Entrepreneurial Leap

The scariest jumps often lead to the softest landings.

Print the business cards before the business exists – it’s about making future reality feel present enough to chase.

From dream to reality:

• May: Printed business cards for a non-existent company
• June: Left corporate job
• July: Launched ATW with multiple clients
• Projected: Seven-figure revenue in first year All with less than $10,000 in startup costs.

Lesson: Sometimes you need to build the bridge as you walk across it.

The Faith Factor

“Pray as though everything depended on God. Work as though everything depended on you.”

This isn’t just about religion – it’s about believing in something bigger while taking full responsibility for your journey.

The Universal Truths

Remember:

1. You’re never too old for reinvention
2. The imposter syndrome doesn’t go away
3. Success requires a healthy dose of delusion
4. Your belief in yourself must outweigh others’ doubt
5. Today’s transition phase is tomorrow’s foundation

The secret isn’t just in asking for what you want – it’s in being bold enough to believe you deserve it.

Keep being delusional enough to believe in yourself until other people can see what you’ve always known was there.

The “smart one” who built their entire identity around being the brightest person in the room.

But life has a funny way of teaching you what really matters, and it’s rarely what you think when you’re young.

The Golden Child Syndrome

Growing up, my intelligence was my currency.

Two-thirds perfect SAT score, top grades without breaking a sweat, advanced classes across the board.

Everyone around me reinforced that this mattered deeply. So naturally, I turned it into my entire personality—until entrepreneurship taught me otherwise.

The Reality Check

Here’s what nobody tells the smart kids: In the real world, no one cares about your SAT scores.

In fact, constantly showcasing your intelligence can actually work against you.

It’s a harsh lesson, but a necessary one.

The Real Success Formula

The true path to success isn’t about being the smartest – it’s about being the smartest about how you work with others:

1. Let others shine. Instead of correcting someone’s mistake, let them discover a better solution. Your silence can be more valuable than your insight.
2. Share credit liberally. The person who helps others succeed often ends up more successful than the person who proves they’re right.
3. Play your cards close. Being underestimated isn’t a weakness – it’s a secret weapon. Sometimes, your best advantage is letting others think they have the advantage.
4. Master strategic humility. The ability to play dumb when necessary is often more valuable than the ability to prove you’re smart. It’s not about diminishing yourself – it’s about elevating the collective.

Remember: Intelligence might get you in the door, but it's emotional intelligence that lets you stay in the room. Sometimes the smartest thing you can do is not show how smart you are.

When Online Becomes Real Life

My real-life friends tried to understand, bless their hearts. One even sent flowers – a sweet but telling gesture.

Why telling? Because there’s a difference between:

• Supporting something you don’t understand
• Actually getting why it matters
• Speaking the language of digital connection

The Perfect Moment That Said It All

Then came the package that changed everything. A Twitter friend (now real-life friend) sent me a box containing 10,000 spoons – when all you need is a knife.

This moment was perfect because:

• It nailed the reference
• It celebrated the milestone
• It showed deep understanding of our shared digital culture

Finding Your People: The Key Points

What really matters in finding your tribe:

• Location is irrelevant (online, offline, book club, Twitter replies)
• They get your obscure references without explanation
• Your weird wins are their wins too
• Inside jokes evolve naturally and hilariously

The Truth About Digital Connections

Your digital family might include:

• The person who likes your 3 AM thoughts
• Your personal meme curator who knows exactly what will make you laugh
• The friend who celebrates your arbitrary milestones
• People scattered across time zones, speaking in GIFs and references

The Bottom Line

Find your people. Hold them tight. And don't be afraid to ask for what you need.

Sometimes your best moments deserve more than polite congratulations – they deserve someone who’ll send you thousands of spoons just to make you laugh.

Remember: In this vast digital landscape, finding people who truly get you is nothing short of magic. The distinction between "online" and "real life" friends? That's so 2010.

Want to be more fit?

Skip the fancy fitness apps and protein powders. Just spend a year living like a healthier person would, and your body will eventually catch up to your delusions of athleticism.

1. Buy groceries like you’re a health influencer (yes, kale goes in everything)
2. Set your alarm for 5:30 AM (whether you get up is another story)
3. Own at least three matching workout sets (wearing them counts as exercise)
4. Talk about your “morning run” so much that you shame yourself into actually doing it
5. Learn to pronounce “açaí” correctly (it’s harder than the actual workout)

Want to make more money?

Time to channel your inner millionaire. Start acting wealthy before your bank account gets the memo, and watch the universe scramble to catch up.

1. Check your investment portfolio as often as you check your ex’s Instagram
2. Use words like “diversification” and “compound interest” in casual conversation
3. Wear clothes that make you look expensive (even if they’re from the clearance rack)
4. Network at events where you feel slightly out of place
5. Practice your “I’m considering my options” face for salary negotiations

Want to be happier?

Forget the year-long transformation and self-help books. The secret to happiness is simpler than you think.

1. Get a puppy (or borrow one – we don’t judge)
2. Order pizza with extra cheese (it’s scientifically proven to be happier than regular cheese)
3. Watch said puppy try to eat said pizza
4. Send puppy photos to everyone you know
5. Create a pizza fund instead of a retirement fund

Remember: Happiness doesn't come from your habits. It comes from cute baby animals & an occasional burst of carbs. While everyone else is trying to optimize their morning routines, you'll be living your best life one puppy snuggle and pizza slice at a time.

As a guest on this empowering platform dedicated to Women That Flourish (WTF), I shared some insights about breaking out of comfort zones, embracing authenticity, and leveraging social media to build meaningful professional relationships.

Listen to the full episode here.

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Danielle Sprouls: Hello, WTF friends, and welcome to Unscripted Pivots. Ever encounter an experience that just left you shaking your head, saying, what the wtf, right? Sure, we all have. But what if you took that unscripted pivot and you transformed it into a moment of empowerment? We are here in this podcast to turn those setbacks into setups. I’m Danielle Sprouls, your host, certified executive coach, and the creator of the WTF Community, where WTF stands for Women that Flourish. And yes, I am the WTF lady.

Danielle Sprouls: This podcast is your ignition. It’s a place to awaken your potential, embrace unscripted changes, and just step into your power with courage and passion. Like you, I’ve navigated life’s unexpected turns, and I completely understand the power of starting over again. Every Wednesday, we’ll be sharing inspiring stories from women just like you, along insights from thought leaders and visionaries in the business, personal growth, spirituality, all of it. And guess what? We are now on YouTube, so be sure to subscribe to my channel at Unscripted Pivots to see the women behind these voices.

Danielle Sprouls: So, are you ready to embody your WTF self and pursue what truly fulfills you? Let’s dive in, ladies. Grab your favorite snack, get comfortable, and welcome to today’s episode of Unscripted Pivots. Hello and welcome to another episode of Unscripted Pivots, where we explore the transformative journeys of women that flourish today. I am thrilled to introduce our guest, and I love this woman, Skylar Romines. Skylar is a powerhouse in the commercial insurance industry and the brilliant founder of ATW Advisors, with a career spanning 17 years in commercial Insurance brokerage, Skylar made a bold leap to establish her own firm, advocating for business owners with unparalleled expertise and integrity.

Skylar Romines: Thank you. That was quite the introduction. Can I just bring you around with me everywhere from now on? That would be awesome. Just come to every meeting with me and do that before we start talking about anything. That would be great.

Danielle Sprouls: And it’s so true, right? All of it’s true and then some. And we’ll dive into all of the greatness that makes you you. I usually start the episodes telling the listeners how I met who, you know, I’m interviewing or chatting with. And we met at a Crew Orange county event. We probably met before. The first recollection of me meeting you was when we were kind of like going in and we were sitting there in that auditorium and there was a panel discussion and you just like kind of popped in and you sat to my left.

Danielle Sprouls: And I was going through some crazy stuff at the moment, but in those five or ten minutes in our whispering conversation, I got to know a little bit about you and what I knew right then and there is, I wanted to know more. You had like, you know, mentioned you had a book going on and that was always, you know, it’s on my to do list. And some things that, you know, you saw on the horizon. And I said, this is a woman on the move and boy, are you on the move. 2024 has brought so many new adventures your way.

Skylar Romines: So, yeah.

Danielle Sprouls: What inspired you after a successful, like 17 year career in commercial insurance brokerage, to start ATW Advisors and tell the listeners how you came to choose that name?

Skylar Romines: Sure. So the name was, you know, something that I thought about for a little while. You go through a lot of different ideas, and then you, you know, you get on the Secretary of State website, or you start Googling and realize, like, I can’t have this name. I can’t have that name. That’s already taken. So there were a few that I really wanted before that that ended up not being options, but I ended up loving ATW and what ATW stands for. Because a lot of people ask, they’re like, do you have partners who are at and w. What does this mean?

Danielle Sprouls: Yeah, sure.

Skylar Romines: And what ATW actually stands for is all the Way. And that kind of represents a few different things for me, right. In terms of how we serve our clients. And kind of our slogan, if you will, is we’re with you all the way. Right? We want to represent your firm in the best possible light. We want to be with you from the ground up, want to be really involved in your core business. And so that’s kind of a critical thing.

Skylar Romines: And then, you know, on a personal note as well, and I don’t share this with as many people, but since we’re here, for me, it also represented, you know, my leap, like you mentioned, from 17 years in corporate America, big brokerage, et cetera, into entrepreneurship. And for me, it was like, we’re doing this all the way, right? We’re burning the boats, so to speak. There’s nowhere to go back to. We quit the job. We’re taking the leap, and we’re doing it. And sink or swim, we’re going all the way. So it represented a few different things for me, and I think it’s really special. So I’m glad you asked that.

Danielle Sprouls: It’s so funny, because I wouldn’t even say that there’s just one or two of us. There seems to be this movement in that direction mostly. I mean, I’m more cognizant of what women are doing than what the guys are doing. Maybe they’re doing this too, but where we’re really coming into our own space and taking our skill sets and our relationships and, you know, building our own fortune. I mean, our own way. Right. And so. And what I’m going to say about that is not at the expense of the companies or relationships that we had intact. It’s more of an expansion than it is a replacement.

Danielle Sprouls: And what I’ve noticed about your journey right out of the gate is all the advocates that you have at your side, including the people that you used to work with, which is a testament to their support in your Journey. Right. So it’s not one of those, like, you know, showing somebody the finger while they’re showing you the door. It was more like, you know what, I’ve got something else to offer and I want to work alongside. So you’re leaving something where you felt inspired and trained and educated and you just, you know, you’re like flying the nest and there’s so much support for you in that space. And that really, really is great to see.

Skylar Romines: Thank you, Danielle. Yeah, that means a lot to me. And it’s something that I was actually really nervous about and had to be really intentional about. Right. Because this kind of niche that I’ve carved out with ATW is something that’s different than what we’ve had in our industry before. And I wanted to be able to represent my prior clients who were asking for this service.

Skylar Romines: And just to get a little bit into the background of what ATW does. We’re different than a brokerage or an owner’s insurance rep firm. So a lot of people will call it insurance consultancy. But it’s really a little bit different than that where we’re truly involved in the client’s core business to a degree that I’ve never seen another firm do before. And I had clients on the brokerage side who were asking for referrals for this for a couple of years. And I kept saying, it doesn’t really exist. Right. No one is doing that.

Skylar Romines: And so finally it got to the point where I started thinking, God, if no one is doing this, someone needs to, and if someone needs to, why not me? Right? And that’s kind of how ATW was born. That mixed with the fact that I’ve always wanted to work for myself, but it was never the right time. And you know, you have these self doubts and there’s always something going on and you wait till this, you wait till that, and then it ends up never happening.

Danielle Sprouls: Hey, everyone, did you know that over 850,000 podcasts are being launched every year? That’s because podcasting is a powerful way to connect with your audience, build your brand and grow your business. And trust me, having a podcast can bring immense value to your business by creating a deeper connection with your listeners and establishing you as an authority in your field.

Danielle Sprouls: I just want to take a moment to give a huge shout out to podcircle and my amazing podcast manager, Kyle Cummings. Honestly, I couldn’t do this without the incredible talent and expertise behind me. Whether you’re thinking about starting a podcast or already have one, but need that extra support from a specialist, podcircle is the way to go. Podcircle not only offers top notch support, but also has its own podcast specifically designed to help both new and seasoned podcasters. So if you’re looking for expert guidance and professional advice, podcircle and Kyle Cummings have got you covered. Check out their website@podcircle.com to learn more and let him know that the WTF lady sent you. Now back to our episode.

Danielle Sprouls: You know, that’s so insightful of you to recognize the gap that existed and to fill it. Right. And so it’s not duplicative in many ways to other things that are going on. I could see where there’s some hesitancy where somebody thinks you may be taking a little bit of a piece of their piece, but the way that you’ve just articulated it shows that it really is not even just like an add on. It’s a necessity.

Danielle Sprouls: And I think that you’re going to be leading the charge in this. There probably will be people that will follow over time because there’s. The demand is going to be that great. But you’re at the forefront. You’re like literally a pioneer, okay, in this space. And that, you know, for that it’s like, you know, it reminds me of the title of your book. So she did. So she did. Right? Let’s morph a little bit into your book.

Danielle Sprouls: So, you know, for those of you listening, this woman is just fascinating and she just rolled out a book. You know, I think it was within weeks of rolling out her company. I mean, 2024 for Skylar has been explosive. Like literally so explosive. The book is fantastic. And getting back to our crew Orange county relationship, a lot of the stories within there are testaments to the journey of the women that were with crew.

Skylar Romines: Sure, you touched on so many different things there, Danielle. So I’m going to try to address them all. But I’ll go back to one thing first, if I can, which I think is really kind of interesting, is we did meet through crew and, you know, I was thinking before we started the podcast today, like, what might come up. You know, you’re always kind of wondering what things you might touch on. And I thought about, like, my first impression of you versus probably what your first impression of me was.

Skylar Romines: And this is something that’s a little bit vulnerable for me to share. And I was kind of blow drying my hair and thinking, like, do I get into this? And then I thought, you know what, like you mentioned, 2024 has been a critical year in my life. I actually just did a Twitter post about this this morning. So it’s funny that you mentioned it, but my life has changed more in the last year, year and a half than it did in the 35 years before that. And I can say that, like, without any question or hesitation.

Skylar Romines: And that includes even the year that I had my twins, you know, almost 11 years ago now, or anything else. You know, any major life event that I’ve gone through doesn’t compare to everything that’s changed for me in the last year. And the thing that really changed, that settled that emotion was just a mindset shift, right? Of just realizing that you can literally do anything that you want to do. You just have to freaking do it.

Skylar Romines: And you have to do it scared and you have to do it lonely sometimes. And you have to do it not knowing, you know, knowing that there’s a beginning and an end, but not being able to see the next stone in the path or even, you know, breaking down the stones and laying them as you go. You have to be willing to kind of solve all these problems in real time and figure out what to do.

Danielle Sprouls: I think. And, you know, I’ve undergone a lot of changes in 2024. As well as, you know, and I think that one of the things that I got comfortable with is making failure my friend instead of my foe.

Skylar Romines: I love that.

Danielle Sprouls: I love that that’s really what it boils down to. And, you know, when you are as experienced as, you know, you, as me, and what we’ve been doing for a long time, and we’ve got a very, like, you know, established, stellar relationship, it is not an easy leap to get down to, oh, my God, I don’t know what’s going on. And to know you’re going to falter and you’re going to get some egg on your face.

Danielle Sprouls: You mentioned Twitter. What did. Is that what you wrote on? So do we still call it Twitter or is it called X? I don’t even know. I mean. And guys, let me tell you, she’s prominent on this site, and from what she has shared with me, just in our casual conversations, it wasn’t one of those things that she necessarily pursued, but she became a little bit of a star in this space.

Skylar Romines: Yeah, thank you. I don’t know as far as I’d go as far as to say a star, but I appreciate that. It’s really weird. I started working on LinkedIn maybe a year and a half ago and just kind of posting regularly. And I had never really utilized social media before, and someone had told me, like, just post every day, post about insurance, post about risk management, post a little bit about yourself.

Skylar Romines: You know, what was the term that they use? 70% value, 30% viral. So basically what that means is, like, give your knowledge, right? The last 17 years of your career that you’ve shared, 70%, focus on that, 30%, just focus on you. Let people get to know you for you, because that’s what people really like on social media, right?

Skylar Romines: You don’t want to be. When you’re building your personal brand, you don’t want to be just this business brand. That’s an important piece of it. You also have to let people see, you know, know, little bits and pieces of who you really are, and that’s how they feel connected with you, and you build real relationships. Right? And that’s critical.

Skylar Romines: So I really started on LinkedIn, and then people kept saying, you know, because my business is largely focused on commercial real estate as well. And people started saying, you have to get on Twitter because there’s this corner of Twitter called Retwit, and you have to connect with people there, and there’s so many opportunities.

Danielle Sprouls: Oh, so you were encouraged?

Skylar Romines: Yeah, I was encouraged by several people, but for some reason when he spoke to me, it spoke differently. Isn’t that funny about life? Like, sometimes we can get the same message from different people, but you hear it from one person better than the other.

Danielle Sprouls: The teacher appears when the student is ready. That’s right.

Skylar Romines: That’s right.

Danielle Sprouls: Okay.

Skylar Romines: And, you know, so I said, fine, I’ll try it. I’ll try it for a month. I’ll try it for three months. I’m not going to put a lot of time and energy into it. I’ll repost. I started by reposting my LinkedIn posts on Twitter. I was like, I’ll do that for a while and see how it goes.

Skylar Romines: And I kind of just like you alluded to. I didn’t expect anything of it. I don’t know how to grow a platform. I’m not a professional in this space in any way. I just kind of got on and, and was being authentic and felt a little bit more comfortable on that platform than on LinkedIn to let more bits and pieces of myself come out versus just the business side. And for whatever reason, you know, I kind of got adopted into this retwit real estate Twitter community pretty quickly. I don’t have a huge following. I mean, I have like 8,500 followers or something.

Danielle Sprouls: No, but that’s, that’s a lot in a short time. But you also alluded I was asking you about it because I’m not on that, that app whatsoever. To tell you the truth, I had the same feelings that you did. And from until recently, I was just on LinkedIn. I mean, that’s where we did business and that’s where we got educated, networked. But you, you did something in New York recently. Like, don’t you. I mean, there’s like, I mean, you’re, you’re more involved than just like you posting by yourself, right?

Skylar Romines: Yeah, but I mean, I did. I got invited to. There was a real estate Twitter gala in New York in April. I got invited to that. I don’t know. It’s a big deal, but it was a huge deal. It was a great opportunity. I met so many amazing people. And I.

Danielle Sprouls: Can I stop you? I’m stopping you right here because you said, oh, I got invited to a real estate Twitter. Okay, we’re gonna call it X gala in New York. And I don’t know why. And I wanna say BS to that, BS to that statement. And we do that so quickly because, you know, you may not yet have fully understood the value that you’re bringing, but that’s a testament to the real, to the reality.

Danielle Sprouls: You bring value. That’s why you were invited, Skylar, because they see you as somebody, something to say, and you make the platform better. You may not be the biggest person on X, yet you’re eligible to Y E T. But I’m going to say, you know, we women tend to downgrade the great things that are happening around us. And when we have evidence outside validation and evidence, we’re like, oh, yeah, no, no, no. Shame on that. Okay, we’re not doing. I do it, too. You just did it. And I want to call BS on it, okay?

Skylar Romines: Thank you. I’m going to say something that sounds a little cheesy here, but it’s the God’s honest truth. And it sounds crazy again, because we’re going back to, like, it’s Twitter, and people write that off so easily. The first three clients who signed with me with ATW were either directly from Twitter or referrals from Twitter. My pipeline before I left my brokerage career was seven figures directly off of Twitter and the community there and some of the friendships that I’ve built there in the last. And I’ve only been on six or seven months.

Skylar Romines: I mean, I haven’t had a long tenure there, but even in just launching the firm, I reached out to a lot of friends who have had entrepreneurial journeys and are a step or two ahead of me. Several of those people who gave me some of the best advice when I was getting ready to make the leap were friends from Twitter. And so, again, it sounds crazy, but kind of this network I’ve built, and it’s almost, you know, I was always a nerdy kid. I didn’t have the best family life growing up. Like, I’ve always kind of been fiercely independent and done everything on my own.

Skylar Romines: And I will say the Twitter and Retwit community, and this is where it gets a little cheesy. Bear with me. But it’s the truth. It’s one of the first times in my life and crew, actually, I would put into this category as well, where I actually feel like I have a community that has, like, engulfed and supported me. And I have so much support. And I, you know, for the first 35 years of my life, never really felt that way or had that. And it’s like the most incredible experience, and you just don’t know where your people are going to come from.

Danielle Sprouls: I mean, you’re just shining. You’re just absolutely. You’re glowing. You’re glowing with gratitude. Not just success. You’re glowing with gratitude. That’s evident to me.

Skylar Romines: Yeah.

Danielle Sprouls: Did you want to talk about anything about when you were younger or anything like that? I mean, it was not easy, like you said. It just wasn’t. You know, we don’t need to dive too much. I mean, I know her. I know her personally. But what I love is that the connections that happen when, like you said on X today, you know, I’m nobody special. Like, I didn’t get. I wasn’t born with a silver spoon. I wasn’t, you know, given a position that was elevated.

Skylar Romines: I joke that I just don’t have a comfort zone anymore because I’ve just. I’ve beaten the whole thing down to a point where it’s just gone. Like, all those walls are knocked down. I don’t know what a comfort zone even is. Right. You just have to. Again, it goes back to being so comfortable with yourself. One example I always give is, don’t give me the person who is at XYZ point in their life or has achieved XYZ success because I don’t know where they started. I don’t know what they did to get there. Give me the person who is so confident in themselves and such a strong and resilient individual that you could drop them off naked in the forest without a phone, without any money, without anything, and they’re gonna claw their way back and figure out how to be successful again. That’s the person I want in my corner.

Danielle Sprouls: Yes, absolutely. And that’s who you are. And you know what? I’ll add to that. You just reek of authenticity.

Skylar Romines: Thank you.

Danielle Sprouls: This is why you have so many allies. And like your army, your Skyler army continues to grow. No, because you are as authentic as it gets. And I like the Raw and the realness. I wanna jump back to the book. Cause I don’t wanna. First of all, everybody go buy that book. It will be in the. It’s on Amazon. It might probably through your website too. It’ll be in the show notes. But I want you to talk a little bit about the women that you chose to interview for your book.

Skylar Romines: Yeah, so I was coming up on my 36th birthday and I had been playing around with this book for a little while and I had a moment where I thought, okay, I need to. I had done the first version of the book. We’ve talked about this a little bit. I’d written the first version of the book with all of my own thoughts and all of the statistics and no stories and you know, first time author learning things the hard way.

Skylar Romines: You know, kind of just throwing yourself into the deep end of the pool and figuring stuff out as you go. You know, big mistake there. If you’re going to interview people for a book and include their stories in the book, interview them first and then backfill the rest of the information around it. But I didn’t do that. I did it the other way.

Skylar Romines: So I started thinking about who am I going to include in here? And had a few people who I talked to personally who I knew I wanted to include. And then I thought, okay, here’s what I’m going to do. Because I got to a point with the book where I’d put just enough time into it that I was sick of putting time into it if I wasn’t really going to do something with it, you know.

Skylar Romines: So I was like, I either need to really decide that I’m going to finish writing this book and I’m going to publish it and it’s going to be a real thing, or I need to walk away from it and rededicate this time and energy that I’ve been putting to this project to something else. Because it can’t just be this dead end. And I kind of, you know, broke down, had a conversation with God. And I know that’s, you know, may not resonate with everyone, but for me, it’s a very important part of my life.

Skylar Romines: And I was like, hey, I need about 30 women who have great stories who are either founders, CEOs, like you said, project managers, surveyors, people who are out in the field, people who are in these male dominated industries who have a story to tell. And I told God, and I talked to God this way, maybe everybody doesn’t, but I said, I need 30 women in the next two weeks or I’m not doing this.

Danielle Sprouls: All right, so did you. Did they write in their experiences or was this like a phone call? How did you collect the information?

Skylar Romines: We did video interviews. I had a couple I met with in person, but I interviewed women from all across the country, even one woman in the uk, so wasn’t able to meet with everyone in person. So most of them were just zoom video interviews.

Danielle Sprouls: So you got to see the body language attached to the story. Yeah, and that must have been powerful because one of my episodes a couple episodes ago, I asked a very simple question to a few women at a couple different events.

Danielle Sprouls: It was really random, the one I was doing and nobody knew. Anyway, I said, if you could go visit your 18 year old self, what would you tell her? And when I had the opportunity to see the facial expressions really, really change, it was something else. So I could only imagine speaking to somebody like, you know, for more than one minute and, you know, sharing the intimacy of that space and even the celebration, the highs and lows that come with them going down, you know, memory lane.

Danielle Sprouls: Thank you so much for coming on. It was a pleasant thank you for tuning into unscripted pivots and joining the WTF women that flourish community today. And when your next WTF moment hits, remember this, you are built to flourish. Please help spread the word, share this episode and if inspired you. A five star review would mean the world to me. It’s a powerful way to help us reach more people just like you.

Danielle Sprouls: In the show notes you will find all guest information and if you’re thinking about working with a coach, I’d love to hear from you. My website is unscriptedpivots.com there you will find not only my calendar, but WTF highlights and resources designed to empower you. Until next time, face challenges head on, knowing you’re meant to flourish through every pivot. See you soon.

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I really don’t want to be the bearer of bad news, but as the resident insurance nerd I feel it’s time to say something…

Related: Key Trends Shaping Commercial Insurance .

This connects to Alternative Risk Financing for Family Offices.

Actually I’ve been saying it on every podcast I’ve recorded the past couple of months too [go listen to learn more about commercial insurance 🫡]

Better to be prepared than surprised, so here goes…

The same way we just witnessed a hard Property insurance market cycle, there have been leading indicators throughout 2024 that a hardening General Liability market cycle is next.

👉🏼 Marsh’s Global Insurance Market Index has now confirmed: commercial insurance rates during Q3 in the US were +3% with Casualty rates +10%

👉🏼 Reinsurers are seeking double digit rate hikes for US Casualty in 2025 renewals.

👉🏼 Along with rate hikes, reinsurers are looking to reduce US Casualty exposure, requiring more detailed data from cedants & reduce coverage limits [Does this SCREAM hard market to anyone?? It should]

👉🏼 Certain industries will be hit harder by increasing GL costs. Look out for Real Estate, Hospitality, Public Entity & Education.

👉🏼 Emerging liability risks in the US including those linked to microplastics, opioids & pfas are adding uncertainty for insurers & reinsurers.

What Does It Mean?

Don’t get caught off guard in the next hard market cycle. It’s not a maybe, it’s coming.

General Liability will be the next challenge. Hopefully your insurance team is already talking to you and strategizing for this.

Passive purchasers of insurance who are still buying ‘the old way’ will continue to be slammed with unexpected increases & shrunken capacity.

How Do We Fix It?

Tort reform could potentially curb the increased loss & nuclear verdict trend, but that doesn’t appear to be an immediate public policy priority.

Data data data + risk management. This will set operators apart from their peers.

It has never been more important to build a strong insurance team & have proactive SOPs surrounding insurance procurement/risk transfer.

With traditional insurance markets becoming increasingly restrictive and expensive, up to 30% of billion-dollar family offices are exploring alternative risk financing strategies.

In this article, we’ll uncover three common types of alternative risk transfer and financing, each providing unique benefits for family offices seeking more flexible solutions:

• High Deductibles
• Captive Insurance
• Self-Insurance

Whether you’re a family office considering alternative risk financing or simply interested in this growing trend, this article offers actionable insights on effectively implementing these strategies while navigating their complexities.

Rethinking Risk Management

The use of captives and self-insurance among family offices is rising in popularity.

Many family offices are exploring or establishing captives, especially as they expand their asset bases and face increasingly complex risks.

This trend is partly driven by dissatisfaction with rising premiums and reduced capacity for coverage in the commercial insurance market.

Others seek tax advantaged solutions or value having a higher degree of control of their own program and loss payouts.

There is no central registry for family offices, largely due to their private nature and the emphasis on confidentiality.

However, surveys indicate that up to 30% of larger family offices (managing at least $1 billion USD) have considered or are actively using captives, though not all have fully implemented them.

Alternative Risk Financing

All forms of alternative risk financing require more ‘skin in the game’ as opposed to the traditional insurance market and can be structured creatively based on each family office’s needs.

It is typically wise to determine the desired level of Risk Retention, and then weigh strategies for risk transfer above that layer.

Some common types of alternative risk transfer and alternative risk financing include:

High Deductibles

• Maintaining a high deductible level with traditional insurance layers placed in excess of the deductible layer.
• Depending upon the deductible level chosen, a captive layer or dedicated ‘self-insurance’ fund may be prudent to address losses the family office will be responsible for under that threshold.

Captive Insurance

• A captive is an insurance company created, owned and operated by its stakeholders. The people in charge of the captive are the ones who benefit from its insurance coverage.
• Captives may include many small to medium organizations of similar size (group captives), or can be made up of one parent company with only related entities, often referred to as a ‘single parent captive’.
• Captive insurance companies purchase reinsurance directly to ensure they have enough capital to pay for large losses.

Self-Insurance

• Self-insurance is often utilized unintentionally, when there is a failure to acknowledge or adequately address certain risks associated with an organization.
• However, formal self-insurance is another form of coverage where there is no insurance policy issued to the insureds.
• According to IRMI, the International Risk Management Institute, self-insurance is “a system whereby a firm sets aside an amount of its monies to provide for any losses that occur – losses that could ordinarily be covered under an insurance program.”
• When an organization takes part in self-insurance, it does not hold an official insurance policy.

Key Takeaways

1. The main difference to note between self-insurance and captive insurance is how each is set up.
2. With self-insurance, the owner sets up a type of savings account where they save money to use when claims arise.
3. Captive insurance, on the other hand, is more formal because it is essentially a small, dedicated insurance company.

Benefits for Family Offices

Self-insurance and alternative risk financing, such as the use of captives, have been increasingly popular with family offices for many reasons.

Some of the main considerations which make alternative risk financing attractive compared to traditional insurance market, include:

Cost Management

• Family offices, which often manage complex and diverse assets, may find traditional insurance policies to be cost-prohibitive.
• By self-insuring, they can avoid premium hikes and the profit margins of commercial insurers, tailoring risk management strategies to their unique needs and potentially reducing long-term costs.
• There is also a cash flow advantage.

Customization of Coverage

• Family offices typically deal with a range of risks, including real estate, art collections, private investments, and family businesses.
• Self-insurance or captives allow them to design customized insurance policies that address these specific risks rather than relying on standard commercial offerings, which may not be flexible enough.

Better Risk Control

• Self-insuring gives family offices more control over how risks are managed.
• With traditional insurance, risk management practices are often dictated by the insurer, who may or may not reward its insureds with premium reductions for increased risk control measures.
• Self-insurance allows these offices to implement their own risk management strategies, potentially leading to fewer claims and more efficient operations.

Tax Benefits

• Captive insurance structures can offer tax advantages when structured properly.
• Premiums paid to captives are often tax-deductible, and under the right circumstances, profits from the captive’s underwriting activities can accumulate at favorable tax rates.

Wealth Preservation

• For family offices, which typically focus on multi-generational wealth, the ability to self-insure can align with their long-term wealth preservation strategies.
• Self-insurance and captives allow them to retain and invest premium funds, rather than transferring those funds to an external insurer.

Investment Opportunities

• Captive insurance can create investment opportunities for the family office.
• Funds accumulated within the captive can be reinvested, generating returns that would not be possible with a traditional insurance premium payment structure.

Greater Transparency

• Self-insurance provides family offices with clearer insight into the true cost of risk.
• Traditional insurance involves a layer of intermediary costs (brokers, underwriters, etc.), whereas self-insurance allows for direct tracking of claims and expenses.

Key Risks and Considerations

There are also potential increased risks and downsides to captives and self-insurance which should be considered prior to making any material changes to an insurance procurement strategy.

Some of these considerations include:

Upfront Costs & Capital at Risk

• Establishing a captive insurance company or implementing a self-insurance plan requires significant upfront capital, legal, and regulatory setup costs.
• The office also bears the responsibility for paying claims and covering losses. Poorly managed risks could deplete the captive’s funds.

Operational Complexity

• Managing a captive or self-insurance arrangement requires expertise in insurance, risk management, and compliance, adding operational burdens to family office staff.

Regulatory Oversight

• Captives are subject to regulatory scrutiny in the jurisdictions in which they are domiciled.
• Family offices must navigate complex legal and compliance requirements, which can be time-consuming and costly.

Higher Administrative Costs

• The family office is responsible for managing the captive or self-insurance program, which includes claims processing, regulatory reporting, underwriting, and other administrative functions that may require additional personnel or outsourced services.

Potential for Unanticipated Losses

• Without the risk-sharing that traditional insurance provides, family offices may be vulnerable to large, unexpected losses, which could negatively impact liquidity and financial planning.

Time-Consuming Management

• Running a captive or self-insurance program requires continuous attention, from assessing risks to managing claims and ensuring compliance with evolving regulations.

Possible Loss of Reinsurance

• While captives can access reinsurance markets, some reinsurers may hesitate to work with newer or smaller captives, limiting the family office’s ability to manage large, unexpected risks.

No Guarantee of Tax Benefits

• While captives can offer tax advantages, they must be properly structured and compliant with regulations.
• Improperly managed captives could face scrutiny from tax authorities, resulting in disallowed deductions and other penalties.
• They are also subject to regulatory change, such as the potential for 831(b) captive regulation in the United States to change in 2025 as being decided by their Congress.

Key Takeaways

1. As family offices increasingly manage larger pools of assets and more complex risks, these alternative risk financing structures can provide an attractive solution to maintain control, reduce costs, and enhance wealth preservation strategies.
2. It is critical to assemble a strong insurance team of internal and external advisors, which allows family offices to make informed decisions about the most cost-effective and efficient strategies for managing risk and preserving wealth.
3. Feasibility studies are important in determining appropriate retention levels and structures for alternative risk financing based on the specific needs of each organization.

Conclusion

As traditional insurance markets continue to present challenges, alternative risk financing strategies offer family offices compelling opportunities for cost control, customization, and wealth preservation.

While the benefits of high deductibles, captive insurance, and self-insurance can be substantial, success depends on thorough preparation and proper infrastructure.

Family offices should approach these strategies not as mere alternatives to traditional insurance, but as sophisticated financial tools that require careful evaluation of their risk profile, operational capabilities, and long-term objectives.

Those who take a methodical approach to selecting and implementing these strategies, supported by experienced advisory teams, will be best positioned to realize their benefits while effectively managing their inherent challenges.

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