A Wise Investment or a Fool’s Errand?
During a meeting with my intern Henna on Friday, I told her, “I’m not a very smart man.” I was half-joking—but only half. I went on to explain that I keep investing more and more money into my business without ever knowing for sure if I’ll see a return. Is that wise? Or am I on a fool’s errand? Honestly, I don’t know.
Here’s one example: this March, my company is hosting an in-person writing conference at the Wylie Center & Tupper Manor in Beverly, Massachusetts. It’s a huge investment of time, resources, and money—about $25,000, by current estimates. That’s a scary figure, especially since I’ve never done anything like it before. But my entrepreneurial spirit won’t rest.
Per our contract, the event is capped at 75 guests. That’s smart in that it limits our exposure—but it also limits our reach. So I’m exploring adding a virtual option. I’ve spoken with an audio/visual company about recording the panels, workshops, and presentations so we can make them available online. The base price for that service? $15,000. And that doesn’t include the extra time, coordination, and marketing to make the virtual experience work.
Is that wise? Or am I creating more challenges without any guarantee of profit?
If you’re an independent author or small publisher, I bet you know this question well: When does investment cross the line into waste? When will these outlays actually turn into profit? Or does it even matter?
When I started, my risks were much smaller—a few hundred dollars here or there, usually to promote my own book. Now I have dozens of titles to support. My investments range from hundreds to thousands—or, for this conference, tens of thousands.
Here’s another example from this week: I just shipped 73 paperback ARCs of The Porcelain Menagerie by Jillian Forsberg to reviewers and bloggers across the country. The breakdown:
73 paperbacks @ $4.25 = $310.25
73 shipping labels @ $4.63 = $337.99
73 custom bubble mailers @ $1.32 = $96.36
Total investment: $744.60
And that’s just the cash cost. It doesn’t account for staying up past midnight packing books, or lugging three heavy boxes across a construction-zone parking lot to the post office. Will those ARCs result in enough sales to cover that? Who knows?
So when do I stop? When it gets too scary? When I decide I’d rather pay myself instead of reinvesting in the business? It’s hard, because I’ve been doing this for years and have yet to show a profit.
But here’s the thing: I don’t make decisions solely based on money. For better or worse. The Porcelain Menagerie is a great novel. The conference is a valuable experience. I care more about providing those things than about what it costs me to do so. I genuinely believe in the value of what we offer.
Henry Ford said, “The highest use of capital is not to make more money, but to make money do more for the betterment of life.” That’s what I’m aiming for.
Will I add the virtual option to the conference? Maybe. Maybe not.
Will I keep investing my time, energy, and capital into myself, my authors, my company? Absolutely—even if it leads to my downfall. Because we’re publishing great novels. We’re offering valuable services. I have an amazing team. I’ll do everything I can to give them more. I’m willing to accept whatever’s left—even if it’s nothing.
If you’re an author, publisher, or entrepreneur, how do you decide when to say yes to an investment—and when to pull back? I’d love to hear your thoughts.
Learn more about my upcoming conference: https://www.historythroughfiction.com/htf-conference




I don't normally post on this site, even though I am a member, but after you did that shitload of work to help me get my HTF submission through your portal at a point where I was ready to smash a computer, I need to say something.
Your commitment is unwavering. And if you are looking far enough down the line, it will be your legacy, regardless of whether it turns a profit or not. And if that is what you care about, then that's all that matters.
My historical novella '1176' did okay on KDP, and at one point was at 4.3 stars, before settling to 4. But it was only selling when I was paying Amazon hundreds (in CAD) to make sure people saw it. And I am writing other stories too, hoping to get traditionally published in one of the magazines or e-zines out there. Hopefully, I'm at least moderately successful, and can end up writing Byzantine Empire historical fiction, which would be my literary legacy, as well as a series of stories set in the Warhammer 40,00 universe.
The reason I am going on like this is that if I have any success, I will have to, in my will, appoint a literary executor, to decide on advertising, etc., in order for my work to keep on generating money for my son.
You have written and published four books of your own, never mind all your other activities. You will have to do the same thing. Probably also with your company, because it WILL grow, because of the amount of WORK you put into it.
Maybe don't try to go too big right away, if you are sure that you are at an at least break-even point with the first one. That will guarantee you the ability to do another one, with more added to it.
But then again, who am I to say, having failed at a couple of businesses?
I wish you the best.
Just to stick my nose in where it might not belong, here's another venue: https://www.uccr.org/craigville
Until about 2010 (?) and for almost 50 years, the Cape Cod Writers Conference was held there. A group of us were "groupies" to what was a magical experience. No hyperbole. Writers, agents, editors, and the general public mingled for a life-long generative experience.
The new folks who took over in the 2010 block bemoaned the lack of AC and sketchy Wifi. To my mind, those are tools one could find anywhere. What one couldn't find anywhere were the connections and inspiration that happened organically.
Still, they moved the conference to a cookie-cutter hotel site. The conference is now just a weekend. Some of the writers who continued to go there reported back that it was never the same. Setting mattered.
The site now has AC and decent Wifi, though in a thunderstorm, if you're in an outer cottage (like mine) you may find yourself asking Joel to come on over to reset the router. That's just Cape Cod.
A small group of us have continued through the years to hold a "Faux Conference" there -- up until recently every mid-August. With climate change, we're shifting to mid-September now.
The summer the debate was on, the then-conference organizer Jackie Loring sat with us and observed that, should the conference move, people would never have the opportunity we all had had, that they would never know what they had missed.
To me, it looks like what you want to build is the kind of writers' community that is sorely needed.