Lessons on launching, funding and marketing a startup

Sharing stories and lessons from two decades of building startups with Diane Tarshis, founder of Startup Distillery (S3E3)

Marin Gerov
The Needle
4 min readMar 21, 2019

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Diane Tarshis is an experienced startup consultant who started her career in the middle of the dot-com boom and is now the founder of Startup Distillery, where she works with companies to help them navigate the muddy waters of their early days.

With two decades of experience from the entrepreneurial trenches, working with founders from all walks of life and industries, we wanted to talk with Diane about the messy beginnings of small businesses. We covered important lessons around launching a startup, such as the importance of having a roadmap and doing extra homework in preparation, we discussed the pros and cons of self-funding versus raising venture capital and when is it a good time to rely on each. We also touched on the topic of marketing and messaging — a topic near and dear to us, since we are in the middle of figuring out how to talk to our target audience.

As usual, you can find a bunch of resources mentioned in this episode with links below, as well as the main topics we covered in the episode.

Topics we cover in this episode:

01:53 — Who is Diane and what she does

04:56 — How Diane approached her first clients

06:36 — How to figure out what to charge

09:20 — The most common problems startups get stuck on

11:05 — The importance of having a roadmap before launch

12:55 — How to convince a stubborn founder to change direction

16:00 — There’s always another way

17:21 — Bootstrapping versus Venture Funding

20:32 — The argument against going all-in on building a business from the start

23:33 — The myth of stress and the blessing of constraints when bootstrapping a side-business

27:20 — The DULO journey so far

33:05 — What to do when your business plateaus

37:41 — Can you apply lessons from one business into a new one

43:27 — The need to appeal to the head and the heart when marketing your business

45:34 — The importance of a clear and succinct message

49:10 — Future plans and project

54:29 — Get in touch with Diane

Useful Resources and Links:

Connect with Diane — twitter

Check out Startup Distillery

Business Model Canvas

The Teaching Entrepreneurship Workshop

Diane’s DIY Business Plan Kit

Quotes:

Always tweaking your pricing

M: How did you get the confidence to charge higher the next time? Did you go through an experimental period when you were testing out different options?

D: Yes. Always. Always tweaking. But…you know, going through the process it was very labor intensive, and so between that and really taking, believe it or not, what my husband said to heart, I really sort of did this calculation. I also did a lot of my own research, you know, in terms of what are other people charging. I think that’s always a good exercise. Something I advise my clients to do to get a sense of what the market could bear. What are other people charging, what do they include in that price, whether it’s a product or a service? Because you may be offering more or less, or something that’s more valuable, or less valuable, and you should really adjust your pricing accordingly.

A roadmap before launch

I try to make sure that there’s a roadmap from the very beginning. That they don’t stall out and get stuck. So the whole idea is to say “ Okay, you know, who are my… what’s my target audience? Who are my… what are my customer segments? Who am I going after?” Stage 1 — stage 2 — stage 3. “How am I planning to reach them?” Stage 1 — stage 2 — stage 3. Based on traction and the reception that they are getting, based on the growth that they are seeing, because it may be that they grow in different areas that they didn’t predict and so they need to do a shift of resources and focus.

There’s always another way

There’s always another way to solve the problem. If you are not reaching people through social marketing… social media marketing plan maybe you need to think more grassroots. Maybe you need to start at a more local level. If it’s a retail shop offering programming on the weekends, bringing families where there’s a story reading, sort of hour every morning to bring families. Or get involved in the community in terms of neighborhood associations. Or, you know… I don’t know… you know, depending on the business there’s always a way. It’s just a matter, to me, of brainstorming ideas. And the other piece that I find is the more you talk about your business to people the more you’ll… you sort of seem to stumble across new ideas. I always sort of wonder if it’s always out there and you are just tuned in because you are talking about it. Or whether talking about it sort of brings everything to you… but, I don’t know.

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Marin Gerov
The Needle

Building DULO, redefining the dress shirt and documenting the process on https://weardulo.com/blogs/origins