Bullish Q&A: How Do I Get Bullish With My New Biz While My Partner Pays the Bills?

getting Bullish While a Partner Pays the Bills-


Hi Jen, I’m about to leave my job, with only a 2 months of expenses saved and few quantifiable skills in my desired field. I will be completely reliant on my wonderful and trustworthy partner for meeting my material needs while I build a career. She has family money, and doesn’t have to worry about supporting us for a little while. But I have given myself two months to start feeding myself, before we hit the road traveling and freelancing. As my partner said, “Well, it sure isn’t conservative.” I am scared. I know if it all went to hell, I could get another job I hate. But I’m trying to leap here! And I tend to take risks all at the same time, rather than one at a time. I guess I’m hoping you can share some stories and tips for people who successfully Get Bullish and Stay Bullish, while unemployed and building a freelance career and temporarily relying on a partner for meeting their material needs. Help!


Interesting! On the one hand, having this kind of support is just what an entrepreneur needs. On the other hand, it can dampen your sense of urgency if you let it. When I was a 22 year old entrepreneur living on Wal-Mart canned vegetable soup (54¢ a can, always there for me), I was literally too angry to speak to women entrepreneurs whose husbands paid their bills. I mean, I don’t have a logical or moral objection to such an arrangement. But as I recently learned from this essay, there is an expression in Russia: “If I’m hungry and you’re full, you won’t understand me.”

It might not be good for your relationship to treat your partner like an investor in your business, because then you’d have to report back to her on how you’re turning her money into more money. And maybe she’d think that was ridiculous, or maybe she loves you so much she thinks all of your business plans are wonderful even when they’re terrible. So maybe treat your partner like an investor in your head, and don’t tell her about it. As in, “I want to sign three clients by the end of the month before Venture Girlfriend gets antsy,” or “Allow me to make a graph in Excel to show how profits, though small, are increasing steadily – that will persuade Venture Girlfriend to continue investing.” Venture Girlfriend might not be very much like your actual partner, which of course is totally okay.

Another consideration – when you have an immediate need to buy food, it’s hard to think big. When I ran my web development firm, I was often chasing after $2K jobs for local businesses while my richer competitors were preparing proposals and presentations for $100K+ projects. They’d have a whole team work for a week, for free, on a spec campaign to try to win the job. I couldn’t afford to chase after those kind of projects. Or maybe I couldn’t afford not to – my model didn’t exactly work. But when your rent is due and you need another pallet of soup, you place another call to Acme Exterminators and try to sell them the $2K website with the printable coupons and maybe a cartoon cockroach on it. (I did once make a website for a tugboat company with an animated tugboat on it. That happened.)


Again, what does Venture Girlfriend want? Does she want you to produce $3K a month ASAP – in which case your model may plateau at $36K/year – or does she want you to use her money to build something much bigger than that, even if it takes a year or three to get going? And, of course: what do you want?

Of interest:

Bullish: What’s Your Business Model? (If You Think You Don’t Have One, You Probably Just Have a Bad One)

Bullish Q&A: I’ve Got a Side Hustle, But Am I Thinking Too Small?

Bullish: Are You Thinking Too Small?

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