And last night after Mass my friends were like come to the after party and I was already yawning and sleepy and woke up early on Saturday but I went and I’m so glad I did, but it means I didn’t get to sleep until 2am. So today when I woke up I was exhausted and decided to skip my first thing this morning. And only go to one event so I could sleep in. And again there was a time when I would have tried to power through and attend all of it.

I’ve been posting here each week about the Site Monitoring service I’ve developed for my Entrepreneurship course: helping seasonal campers at the park I manage keep an eye on their trailers over the winter when the park is closed.

At this point, there’s not much new to report. Spring is here, the snow has mostly melted, and campers are generally able (and eager) to get back into the park and check on things themselves while they wait for opening at the end of the month.

So this week, I thought I’d reflect on an experience I had at an earlier stage of this project.

At the time, I was considering the practicality of offering a service to clear snow from trailer and patio enclosure roofs. I realized liability insurance would be necessary because there are a lot of ways to damage these structures when removing snow from their roofs. I called my auto insurance provider for a quote, and my agent estimated coverage would cost $3500 to $4000 per year if the underwriter didn’t reject the idea outright. Instead the underwriter wanted answers to the following questions:

What experience do you have with rooftop snow removal?

What risk management procedures do you use?

Where is the snow deposited after removal?

What types of locations are you working on?

How do you prevent damage to the roof?

How many properties do you expect to service?

Do you use any heat in the removal process?

I had good answers for most of these questions, but one in particular exposed a gap in my preparedness.

I could provide a reasonable answer for the question about where the snow would be deposited. Last year, I did have to remove some snow piles I had made from shovelling roofs because they were putting pressure on doors and windows.  However, since people generally aren’t walking in these spaces these accumulations are less of a concern than they would be in a residential setting with regular foot traffic.  A contractor I know told me he avoids this type of work because if he were to shovel a roof leaving snow on a sidewalk, it might turn to ice and even months later, someone might slip and sue.

The question about risk management was the one that made me realize I was underprepared.  My “system” last year had been informal: check inside the trailer to guess where vents and AC units are, avoid scraping right down to the roof, and stick mostly to patio enclosures where there’s less to damage. I also hadn’t really considered the risks to my own safety from working at heights.

It became clear that managing risk would be a major undertaking. Given the estimated cost of insurance and the timing (early February), I would have had to seriously hustle just to break even. I chose not to proceed pursue a quote and instead pivoted to the more manageable Site Monitoring idea.

Winter is winding down, and with it, the narrow window of opportunity for WinterWatch, my site monitoring service for campers storing trailers at the seasonal RV park I manage.

If I had launched earlier, I likely could have captured more demand. My survey showed strong interest.

But I hesitated. especially when pivoting from rooftop snow removal to site monitoring.

Part of that hesitation was strategic. I abandoned making snow removal my focus when I realized the necessity and prohibitive cost of liability insurance.  The underwriter’s questions made it clear this couldn’t be a casual side hustle.

Part of that hesitation had to do with my capacity. With my other commitments, I had to ask myself: If I were to advertise to the entire park population instead of the smaller group of social contacts I surveyed, could I realistically meet the demand?  I’m not sure I could.

If I had insured myself, I could be very busy now shoveling roofs.  The current weather is exactly when snow loads can become dangerous. We’ve had heavy accumulation, a thaw, and now a freeze. If more snow falls on top of that dense base, weights could become destructive. Using a snow load calculator a camper shared, we estimated that one foot of snow can equal roughly 20 lbs per square foot. Across a trailer roof, that adds up to thousands of pounds.

I’ve now begun advertising to the seasonal campers I surveyed. I’ve made it clear I won’t perform rooftop removal due to liability concerns. Instead, I’m offering a $30 WinterWatch package: hike in, photograph snow accumulation, and clear sheds and trailer slide-outs that are the most vulnerable to snow weight and are safely reachable from the ground.

Smaller, but safer.

There have also been unexpected gains.

Seasonal campers recommended me to nearby homeowners who were away on vacation. I shoveled their driveway four times and earned $120. That forced me to add travel expenses into my budget, something I had originally planned to avoid.

Another surprise came when an Amazon package was delivered to the park because a camper mistakenly used their summer address. I shipped it to them via UPS, and they paid me $20 for the service.  It was really a tip, but I’m counting it as ancillary revenue.  It made me realize there may be other small income opportunities connected to site monitoring and off-season support.

One insight stood out to me this week. A friend of mine mentioned wanting to start a side business to supplement his income.  I asked him when he would find the time on top of his 40-hour work week and family commitments. Service businesses trade time for money. That’s challenging alongside a full-time role. We talked about how an ideal side hustle would involve selling a niche product rather than selling hours. A merchandising business could scale better because it isn’t as directly tied to being physically present, although it introduces new risks like storage needs and unsold inventory.

What else I’ve learned:

I had what looked like a promising idea for my Entrepreneurship term project: a rooftop snow removal service for seasonal campers at the RV park I manage. I surveyed a segment of campers and confirmed meaningful demand. Pricing above $90 per hour seemed realistic, and the revenue potential was attractive.

But once I factored in estimated insurance premiums of $3,000–$4,000 per year to cover liability and safety risks, I realized this idea was unfeasible within the constraints of this course.  Not only would I exceed the $50 seed funding assumption, I would also need to work 30-40 hours just to break even on insurance.   With no guarantee of sufficient snowfall, plus school commitments and other responsibilities, the risk of losing money became very real.

So I pivoted to something smaller and safer: a winter property monitoring service.

This involves checking trailers after major snowfalls and windstorms, watching for visible issues such as excessive snow accumulation or fallen tree limbs, alerting owners to concerns, and sending photo updates. I may occasionally charge a small group of friends for limited snow clearing, but only from the ground using an extension roof rake. I’ll invest my $50 seed money toward that too and expect to quickly recover my small capital investment through initial service revenue.

There’s no need for additional financing at this smaller scale.

Still, it’s worth imagining what this business might look like if I tried to fully meet the demand for rooftop snow removal that my survey revealed.  I would need at least the $3000-$4000 in start-up capital required for insurance.  In an average winter, $10,000 would be a reasonable estimate of gross revenue from customers within the park.  To justify my investment in insurance, I would likely feel pressure to hire staff and expand beyond the park. That would require additional spending on advertising, equipment, and transportation.

If I chose to scale this business, I would start with my own money. I would hesitate to seek “love money” from family or friends. wanting to avoid financial strain spilling into personal relationships.  Also, I would prefer not to give up equity when only modest profits are available, and maintaining control helps protect relationships with my potential customer base.  This business doesn’t have the sort of growth potential or originality that would attract angel investors or venture capital.  Crowdfunding might be possible, given the enthusiasm expressed in the survey. Still, I would be cautious about taking on debt, since revenue depends heavily on snowfall, something I can’t control.

If lenders were to evaluate my loan credentials, the assessment would be mixed. My professional profile is strong: as park manager, I understand the customers and the operating environment. But the project’s viability is limited: my survey confirmed demand exists, but weather unpredictability threatens profitability and there are few meaningful efficiencies to be gained as economies of scale.  Although my credit is good, my financial strength is limited by modest revenue projections.  I would probably be better off using personal savings for start-up costs, rather than pledging assets to guarantee a loan for a small, weather-dependent operation.

If this sort of snow removal business were to grow, its growth should be financed by reinvesting earnings rather than relying on outside capital.

I sensed strong demand for a small business removing snow from the roofs of trailers and patio enclosures at the seasonal RV park I manage. Campers worry about heavy snow loads damaging their trailers and patio enclosures.  I did some of this work informally last year, and people were more than willing to pay.

So I did some market research for my Entrepreneurship term project.

I sent out surveys to 42 seasonal campers within my social network and received 26 responses.  The survey confirmed demand exists and people would pay.

Conservatively applying the survey results to the wider customer base suggests that I could potentially serve more than 25% of the park’s 200 seasonal campers - but could I realistically manage that amount of work?

Encouragingly, 75% of respondents said they would accept pricing above $90 per hour. Based on prior experience and that feedback, $100 per hour felt reasonable and competitive.

I estimate about one hour to clear either a trailer or a patio enclosure. If half of potential customers wanted one structure cleared and the other half wanted both, total revenue could approach $7,500 for roughly 75 hours of work. Under ideal snowfall conditions, that’s meaningful side income but also an awful lot of work to fit in between my other commitments.

I also recognized the personal safety risks involved in climbing ladders and working on roofs, as well as the potential for accidental damage when shovelling snow from trailers. Several experienced individuals I surveyed reached out to express concerns about my liability exposure and urged me secure insurance coverage before undertaking this type of work.

I contacted my auto insurance provider to ask about coverage for rooftop snow removal. While waiting for underwriter approval, my agent estimated premiums between $3,000 and $4,000 annually, and approval wasn’t guaranteed.

At $100 per hour, that’s 30–40 hours of labour just to cover insurance before making a dollar of profit.

And the course project assumes $50 in seed funding.

I went from being excited about the idea to having to accept that it was unfeasible.

The Pivot

After talking it through with my instructor, I decided to shift my focus.

The demand my survey identified wasn’t just for snow removal - it was for peace of mind. So, I’m pivoting to something smaller and safer: a winter trailer and site monitoring service. Within the context of the course, it’s the smarter move too.

This service would involve:

Checking trailers after major snowfalls and windstorms

Watching for visible issues such as excessive snow accumulation and fallen tree limbs

Alerting owners about concerns

Sending photo updates

Drawing a Line (in the snow)

I may occasionally charge a small group of friends for snow clearing, but I am drawing a firm boundary around what this business is.

I am not advertising rooftop snow removal. I am not building a commercial service around climbing ladders onto trailer roofs. The insurance requirements alone make that impractical within the requirements of this course.

Operational Reality

From an operational standpoint, this monitoring service will be simple.

I already spend time cross-country skiing and snowshoeing in the park during the winter  Now, I will plan my routes around my monitoring responsibilities.

I don’t require any inventory.  I’m generating core resources internally -my time, my access to the park, my ability to document and communicate. I already own most of the tools I'll need: a smartphone, snowshoes, cross-country skis. I will advertise among a group even smaller than the one I surveyed. Even without any further solicitation, I expect I'll hear from some of the survey group.

If I decide the circumstances are appropriate for limited, low-risk snow removal, I have the snow shovels required. I will put my $50 in seed money toward purchasing an extension roof rake so that any roof clearing can be done safely from the ground.  I have priced suitable models at around $100 and would contribute the remaining balance as a small personal capital investment, expecting to recover that amount quickly through service revenue.

I’ll operate solo, handling inspections, communication, and recordkeeping myself. No special trade license is required for monitoring services. Most importantly, this can realistically be launched within the remaining 6 weeks of the course.

What I Learned

Having to pivot this way helps me understand that while entrepreneurship involves spotting opportunity, it also requires stepping back when the numbers and risks don’t support scaling up.