I‘m going to keep a startup diary here to share the ups and downs of a tech startup, old lessons applied, new lessons learned and how things progress. If you’ve got a startup - or a business you’re growing - I’d love to hear what you are up to.

I’ve spent the last week double checking if I really want to go full throttle with a new business this year. Each time I share my business idea with colleagues, they are encouraging, excited even. Some talk about their interest in investing as well which I take as a good sign and vote of confidence.

I’ve never before asked for money from friends and family - the typical “Friends and Family” round that many tech startups go through prior to a more official angel round. Not that I didn’t believe in what I’ve built in the past but usually because I’ve started service businesses that mostly ran - and grew - on revenues.

Thinking about asking for money from people I know does give me a little bit of heartburn. I have every confidence that this business will pay off, but it is still scary to put relationships into the business mix. I’ve thought of using a site like Kickstarter to crowdsource funds (crowdfunding) before I incorporate - while it is still just me and a personal project. I’ve also looked Profounder as another crowdfunding site but one that funds for-profit businesses. Both have an excellent process and system to facilitate soliciting and receiving funds from people you know, including through your social networks.
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I’ve always struggled with keeping client estimates and invoices straight. I forget to invoice or invoice really late which means I get paid much later than anticipated. Recently, I accidentally numbered my invoices incorrectly and had to go back to clients asking them to use a different invoice number. Frustrating. And unnecessary, even for the chronically discombobulated mommy-brained person like me.

While I’m still toying with the idea of turning all my billing over to a bookkeeper (probably a smart idea, but I’m chronically slow at outsourcing things), I’ve taken the plunge and payed for an online service that is whipping me into shape. I thought I’d share this with you if estimates and invoices are under your purview but making you a little crazy.

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