{"id":970,"date":"2022-11-22T15:37:14","date_gmt":"2022-11-22T15:37:14","guid":{"rendered":""},"modified":"2025-06-24T20:52:25","modified_gmt":"2025-06-25T04:52:25","slug":"startup-founders-four-questions-insidevc","status":"publish","type":"post","link":"https:\/\/www.microsoft.com\/en-us\/startups\/blog\/startup-founders-four-questions-insidevc\/","title":{"rendered":"Four questions startup founders should ask investors &#8211; #InsideVC"},"content":{"rendered":"\n<p class=\"wp-block-paragraph\"><em>This is the second of four posts offering practical advice to early-stage startup founders from an entrepreneur turned venture capitalist. <a href=\"https:\/\/shriftman.medium.com\/\" target=\"_blank\" rel=\"noopener\">Jonathan Shriftman<\/a> is a partner at <a href=\"https:\/\/xcap.vc\/\" target=\"_blank\" rel=\"noopener\">Expanding Capital<\/a>, a growth stage VC fund that invested in companies like Coinbase, Cameo, Classpass, Postscript and Astra Rockets. Previously Jonathan founded Humin, an AI-powered address book that was acquired by Tinder, and <a href=\"https:\/\/www.solebicycles.com\/\" target=\"_blank\" rel=\"noopener\">Sol\u00e9 Bicycles<\/a>, the first direct-to-consumer online bicycle retailer.<\/em><\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><em>You can read the first part of this series here:<\/em><\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li class=\"wp-block-list-item\"><em><a href=\"https:\/\/www.microsoft.com\/en-us\/startups\/blog\/early-stage-founders-insidevc\/\" target=\"_blank\" rel=\"noopener\">Advice for early-stage founders<\/a><\/em><\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\"><em>Fundraising can be a stressful time. We asked Jonathan for examples of questions startups should pose to venture capitalists when trying to evaluate a potential investor.<\/em><\/p>\n\n\n\n<p class=\"wp-block-paragraph\">When you\u2019re out there trying to raise money from investors, VCs will ask you all the questions. But don\u2019t forget that there are some questions you need to ask your potential investors:<\/p>\n\n\n\n<h2 class=\"wp-block-heading\">1. Does the VC lead?<\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">Lots of VCs may be interested in investing in your round but they can\u2019t all lead it. The lead investor will be the one that sets your startup\u2019s valuation and will be your closest strategic partner moving forward. They will also likely be your largest investor.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">If a fund indicates that they want to be your lead investor, then there is an important follow up question.<\/p>\n\n\n\n<h2 class=\"wp-block-heading\">2. What percentage of their fund are they investing in your startup?<\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">Sometimes funds make small investment relative to the total amount they are managing. They\u2019ll want to keep a close eye on you. But, generally speaking, you want a fund to make a larger investment in your company.<\/p>\n\n\n\n<h2 class=\"wp-block-heading\">3. How much does the fund leave for follow-on funding rounds?<\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">A good rule of thumb is a 4:1 ratio. If a VC invests $1M into your company now, they might want to invest $4M in your next round either as an up-round or for additional support.<\/p>\n\n\n\n<h2 class=\"wp-block-heading\">4. Ask for references from other startup founders<\/h2>\n\n\n\n<p class=\"wp-block-paragraph\">You should make sure to ask the VC for two references. Ask them for a reference to a founder who did really well, but also ask them for a reference to a founder who went out of business. You want to ask that second founder how the VC treated them when their company wasn\u2019t doing so well.<\/p>\n\n\n\n<figure class=\"wp-block-embed is-type-video is-provider-youtube wp-block-embed-youtube wp-embed-aspect-16-9 wp-has-aspect-ratio\"><div class=\"wp-block-embed__wrapper\">\nhttps:\/\/youtu.be\/V8BUq4WBQQk\n<\/div><\/figure>\n\n\n\n<p class=\"wp-block-paragraph\"><em>For more tips from venture capitalists and access to the resources you need to see your startup through its next challenge, <a href=\"https:\/\/foundershub.startups.microsoft.com\/signup\" target=\"_blank\" rel=\"noopener\">sign up today to Microsoft for Startups Founders Hub<\/a>.<\/em><\/p>\n\n\n\n<p class=\"wp-block-paragraph\">&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>The lead investor will be the one that sets your startup\u2019s valuation and will be your closest strategic partner moving forward.<\/p>\n","protected":false},"author":63,"featured_media":972,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"ms_queue_id":[],"ep_exclude_from_search":false,"_classifai_error":"","_classifai_text_to_speech_error":"","_alt_title":"","ms-ems-related-posts":[950,262,260,175],"footnotes":""},"post_tag":[],"content-type":[201,728],"job-role":[],"topic":[734,72],"coauthors":[609],"class_list":["post-970","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","content-type-founder-advice","content-type-news","topic-guidance-and-development","topic-venture-capitalism-and-fundraising"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.2 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Four questions startup founders should ask investors - #InsideVC - Microsoft for Startups Blog<\/title>\n<meta name=\"description\" content=\"Venture capitalist Jonathan Shriftman 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