Chapter Three
Simon
I didn’t work on Saturday. After Liam’s pointed conversation about my assistant situation a few days ago, I was determined to prove—to myself at least—that I had everything under control. Even without Sarah.
Instead, I spent the entire day pacing my apartment, mentally cycling through all the work piling up on my desk.
Emails I should be answering. Reports I should be reviewing.
Calls I should be returning. All the work that wasn’t getting done because I was only one person and it was too much for me to keep up with.
Maybe Liam had a point. I didn’t like admitting that, but I was man enough to acknowledge when I was wrong. At least privately. I wasn’t about to actually tell Liam he was right. Didn’t want my brother getting too cocky.
It was early evening when a knock sounded at my door.
“Come in,” I called from the kitchen, grabbing a couple of beers from the refrigerator as my good friend Kurt Seager walked in. He had a six-pack tucked under his arm, and I took it from him as I handed over one of the cold bottles I’d just retrieved for the two of us.
“You were almost late,” I said as we moved into the living room, where pre-game analysis had been droning on for the past hour.
Kurt’s brother, Miles, played hockey for the New York Lynx, and I was lucky enough to attend home games with Kurt fairly regularly.
But tonight’s game was in Virginia, which meant we’d be watching on my flat screen with cold beers and pizza on the way.
“I didn’t realize you were watching the clock.” Kurt twisted the cap off his beer, his tone dry. “Were you worried I was going to stand you up?”
I punched him in the shoulder, nearly making him spill his drink. Kurt was one of my oldest friends, and I was used to his sense of humor.
“I wasn’t worried.” I settled onto one end of the couch while he claimed the other. “I just figured you were busy with some woman again.”
Kurt groaned. “That was one time. And it was like three years ago. I don’t pick up women like I used to.”
“Getting too old to be a player?”
This time he punched me.
“What about you?” He raised an eyebrow. “Haven’t seen you with a woman in a while. You take a vow of celibacy or what?”
I chuckled, then took a long pull from my beer. “I’m busy. I spend too much time at work to get serious with anyone.”
Not that I was living like a monk. When I needed to blow off steam, finding a willing partner was never a problem.
The women I ended up with were usually from the same circles I’d grown up in—socialites who recognized the Powers name and everything that came with it.
They weren’t interested in me, not really.
They were interested in the family money, the connections, the lifestyle.
And honestly? That suited me fine. I didn’t have time for anything real.
Didn’t have the bandwidth for emotional entanglements or the complications that came with them.
Casual and brief worked for everyone involved. No expectations. No disappointments.
The game started, and conversation dropped away as we focused on the players. The first period was intense—Miles was having a hell of a night—and when the pizza arrived, we demolished a large supreme between us while working through a few more beers.
When the period ended and commercials flooded the screen, one of the first ads was for an athletic wear company. Sleek. Modern. Exactly the kind of brand we’d tried to build eight years ago.
My jaw tightened at the unexpected reminder.
I glanced at Kurt, but he was typing away on his phone, seemingly oblivious.
We never talked about the company. For my part, even thinking about it felt like pressing on a bruise that never fully healed.
My first real failure. The first business I’d really poured my heart into, only to watch it crumble because I’d trusted the wrong person.
“You know, I saw Chuck a couple of weeks ago,” Kurt said suddenly, confirming that I wasn’t the only one with the past on his mind.
Chuck had been our third partner in that venture—older, more experienced, the one we’d trusted to handle production while Kurt and I focused on marketing and growth. We hadn’t stayed friends after everything fell apart.
“He was at an art gallery opening,” Kurt went on. “Hanging around some artist with his tongue practically dragging on the floor behind him.”
I would’ve laughed at the image if thoughts of Chuck didn’t make my blood pressure spike. “Did you talk to him?”
Kurt scoffed. “Hell no. I’ve got nothing to say to that dick.”
I shook my head slowly, the old anger stirring in my chest. “I still can’t believe what he did to us. To the company.” My voice dropped, rough with something I didn’t want to examine too closely. “I can’t believe I trusted him.”
We’d been young and hungry, fresh out of college with more ambition than sense. Chuck was a decade older, seasoned, with the kind of business experience that made him seem like a sure thing. We’d handed him the keys to production and quality control, confident he knew what he was doing.
Instead, he’d cut corners on materials to pad his own margins.
Skimmed money off the top when he thought we weren’t looking.
By the time we caught on, our reputation was already tanking.
Reviews were brutal. Returns piled up. And our fledgling company—the thing we’d built from nothing—collapsed under the weight of his greed.
A bigger, more established business might have weathered the storm. We didn’t stand a chance.
“Same,” Kurt agreed, his voice flat. He finished his beer and stood. “You want another one?”
“Yeah.”
He headed for the kitchen while my thoughts lingered on Chuck and the sting of watching everything I’d worked for fall apart. I’d been so proud of that company. So certain we were building something real.
And then it was gone.
The memory made me think of Carla. Wasn’t that the same mistake I’d made with her? Trusting someone because of their experience, their credentials, their confident assurances—only to be blindsided by incompetence a second time?
“Well, I’ve learned my lesson now,” I muttered to myself, just as Kurt walked back into the room.
“What’s that?” He handed me a fresh beer and settled back onto the couch.
I leaned into the cushions, scrubbing a hand down my face. “Just thinking about how that old mess is still rattling around in my head.” I paused, then decided to just say it. “You know how I’ve had trouble keeping an assistant?”
Kurt’s expression shifted. “Don’t tell me you fired another one.”
I nodded. “Couple of days ago.”
He let out a low whistle. “Damn, Simon. It’s starting to seem like you’re sabotaging yourself.”
The defensive response rose automatically—high standards, inadequate employees, the same justifications I’d given Liam. But while all of that was true, I knew it wasn’t the real problem.
“I have a hard time trusting people,” I admitted, the words scraping against my pride on the way out. “In business, I mean. I can’t shake the feeling that if I don’t maintain total control over every aspect of the company, it’ll all come crashing down again. Just like last time.”
If anyone would understand, it was Kurt.
We’d both lost our first business, both had our confidence shaken by Chuck’s betrayal.
But Kurt had been in an even worse position than me.
I had family money to fall back on—a trust fund that cushioned the blow.
Kurt had invested everything he had. When the company went under, he lost it all.
He was doing well now, working as a wealth manager at a prestigious firm, but I knew those early years after our failure had been brutal for him.
Kurt was quiet for a moment, turning his beer bottle slowly in his hands.
“You know what happened wasn’t your fault, right?
Chuck screwed us over. That’s on him.” He met my eyes, his expression unusually serious.
“But I’m going to be honest with you. If you keep firing assistants and trying to do everything yourself, you’re going to miss something.
A detail. A deadline. And when that happens, when you inevitably drop a ball, that will be your fault. ”
I hated that he had a point. Just like Liam.
“You know anyone who could handle my bossy ass?” I asked, trying to lighten the mood.
To my surprise, Kurt didn’t laugh it off. His expression turned thoughtful, and he studied me for a long moment.
“Actually… I just might.”
I set my beer on the coffee table and leaned forward, elbows braced on my knees. “Who?” I asked curiously.
Kurt placed his own bottle down and shifted on the couch to face me directly. “Now, don’t say no immediately—”
“You’re not off to a great start.” I scowled, immediately suspicious.
“Just keep an open mind, okay?” He held up a hand, preemptively cutting off my objection. “I think you should consider hiring my sister. Raina.”
I stared at him. Kurt was my best friend. And I had a well-documented tendency to alienate my assistants before inevitably firing them. Hiring his sister seemed like a guaranteed way to destroy our friendship.
“I’m pretty sure that’s a terrible idea,” I said flatly. “In case you haven’t noticed, I’m difficult to work for.”
Kurt smirked. “Raina’s tough. She can handle it.”
I’d known Kurt for years, but somehow I’d never actually met Raina.
She was a few years younger than us, and our paths had simply never crossed.
I’d heard bits and pieces about her over the years, enough to know she’d worked as an executive assistant before, which was promising.
But I also knew that job had ended badly.
Kurt had mentioned she’d been fired under questionable circumstances and hadn’t been able to land another position in six months.
Six months was a long time to be unemployed. There had to be a reason.
“I don’t know…” I shook my head slowly. “If she’s been out of work for half a year, that’s a red flag.”
“She got screwed over by a vindictive boss,” Kurt said, an edge creeping into his voice. “The guy’s been actively sabotaging her job search. It’s not a reflection of her work.”
That gave me pause, but it didn’t erase my concerns entirely.
Beyond the employment gap, there was still the matter of Kurt.
If I ended up firing his sister—and based on my track record, that wasn’t exactly an impossibility—would he resent me for it?
Would it poison a friendship that was incredibly important to me?
But maybe… maybe that was exactly what I needed.
Maybe if I had Kurt’s friendship hanging in the balance, I’d be forced to actually give his sister a fair shot.
A real chance to prove herself instead of looking for reasons to push her out the door.
It was risky. If she turned out to be terrible at the job, I’d be stuck in an impossible position.
But I was already stuck. My workload wasn’t getting smaller, and I was running out of options. Either I gave Raina a chance, or I called a temp agency and ended up with some random person who might be completely unqualified. The thought of that made my skin crawl.
I turned the idea over in my mind, examining it from every angle. “How about a ninety-day probationary period?” I finally said. “We see how things go for three months. If it’s not working, for either of us, we part ways professionally, no hard feelings. And you don’t hold it against me.”
Kurt studied my face for a moment, then nodded slowly. “Fair enough. I’ll let her know.”
“Fine.” I picked up my beer, already half-regretting the decision. “But I’m warning you, I’m not going to go easy on her just because she’s your sister.”
Kurt’s smirk returned. “I wouldn’t expect anything less.”
The second period started, pulling our attention back to the game. But my mind kept drifting to this sister I’d never met, this unknown variable I’d just agreed to let into my carefully controlled professional life.
I told myself it was just ninety days. Three months to see if she could handle the pressure, meet my standards, and prove she was worth trusting.
Realistically? I expected her to be gone before the probation period ended. If she even lasted that long.